Category: 681465-85-0

Application of 681465-85-0, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 681465-85-0, name is Methyl 4-amino-3-isopropoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The aryl carboxylic acid monomer (6 mmol, comp. 4-6), Mukaiyama reagent (6 mmol) and Et3N (12 mmol) were dissolved in an anhydrous dichloromethane (100 mL). The solution was refluxed for 15 min. under N2. Then a solution of the corresponding arylamine (5 mmol, comp. 7-9) in an anhydrous dichloromethane (20 mL) was added to the reaction mixture and resulting solution was refluxed for 2 days. The solvent was evaporated under vacuum and the residue was subjected to the column of silica gel using the mixture of hexanes/ dichloromethane (2:3) as an eluent to give amide coupling products in moderate to good yields. Note: for the synthesis of 18, 2.5 eq. of corresponding aryl amine over 2-methoxyisophthalic acid was used.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-amino-3-isopropoxybenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Kulikov, Oleg V.; Incarvito, Christopher; Hamilton, Andrew D.; Tetrahedron Letters; vol. 52; 29; (2011); p. 3705 – 3709;,
Ester – Wikipedia,
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Related Products of 681465-85-0, The chemical industry reduces the impact on the environment during synthesis 681465-85-0, name is Methyl 4-amino-3-isopropoxybenzoate, I believe this compound will play a more active role in future production and life.

To 10-Chloro-2-cyclopentyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-8,10,12-trien-5-one (Intermediate 1, 190 mg, 0.68 mmol) was added a solution of Methyl4-amino-3-propan-2-yloxy-benzoate (Intermediate 71, 145 mg, 0.69 mmol) in ethanol (4 mL), followed by water (12 mL). Concentrated hydrochloric acid (36%; 140 mul) was added and the reaction heated to 80 C., with stirring, overnight. The reaction was allowed to stand and cool overnight, before evaporating ethanol. The aqueous residue was diluted to 40 mL with water and the solution basified to pH 9 by addition of a few drops of aq. ammonia, The resultant emulsion was treated with a little brine and extracted with DCM (2¡Á30 mL). The biphasic mixture was poured into a PTFE cup and the organic phase allowed to drip through under gravity. Evaporation of the organic phase afforded an amber gum, which was purified by flash chromatography on silica (40 g Si cartridge; ISCO companion), eluting with a rising gradient of 25-100% ethyl acetate in iso-hexane. Product containing fractions were combined and evaporated to give a colourless gum which was triturated with a small amount of diethyl ether and the resultant solid collected by suction filtration and dried to afford the title compound as a white solid (132 mg, 43%)1H NMR (400.132 MHz, DMSO-D6) delta 1.36 (d, 6H), 1.58-1.77 (m, 6H), 1.95 (m, 2H), 2.60 (m, 2H), 3.18 (s, 3H), 3.64 (m, 2H), 3.83 (s, 3H), 4.77 (m, 2H), 7.53 (m, 1H), 7.57 (m, 1H), 7.78 (s, 1H), 8.10 (s, 1H), 8.51 (d, 1H); MS m/z 452 [M+H]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4-amino-3-isopropoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; US2008/9482; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 681465-85-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 681465-85-0 name is Methyl 4-amino-3-isopropoxybenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

4-(2-(Benzyloxy)-3-isopropoxy-4-nitrobenzamido)-3-isopropoxybenzoate 2-Benzyloxy-3-isopropoxy-4-nitrobenzoic acid (51.5 mg, 0.16 mmol) was dissolved in CH2Cl2 (8 mL) and preactivated with Ghosez’s reagent (66.0 muL, 0.50 mmol) for 3 hours at 40 C. 3-Isopropoxy-4-aminomethylbenzoate (0.12 g, 0.55 mmol) was dissolved in CH2Cl2 (8 mL) and N,N-diisopropylethylamine (DIPEA) was added (0.20 mL, 1.12 mmol). The solution containing the acid chloride was then added and the reaction mixture stirred for 2 days at 40 C. The solvent was then removed and the crude product was purified by preparative HPLC (RP-18; run time 100 min; H2O/MeCN=100:0?0:100; tr=80 min) providing the title compound (56.9 mg, 0.11 mmol, 68%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) delta 10.33 (s, 1H-NH), 8.55 (d, J=8.5 Hz, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.70 (dd, J=8.5, 1.7 Hz, 1H), 7.59 (d, J=8.7 Hz, 1H), 7.57 (d, J=1.7 Hz, 1H), 7.25-7.12 (m, 5H), 5.25 (s, 2H), 4.75-4.67 (m, 1H), 4.67-4.59 (m, 1H), 3.93 (s, 3H), 1.40 (d, J=6.2 Hz, 6H), 1.28 (d, J=6.0 Hz, 6H) ppm. 13C NMR (100 MHz, CDCl3) delta 167.0, 161.4, 151.1, 147.9, 146.1, 145.2, 134.1, 132.9, 132.9, 130.0, 129.4, 128.7, 125.79, 125.6, 123.3,120.1, 119.5, 113.3, 78.9, 77.4, 71.7, 52.3, 22.6, 22.1 ppm. HRMS (ESI): Calculated for C28H31N2O8 (M+H+: 523.2080. found: 523.2075.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-amino-3-isopropoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; HELMHOLTZ-ZENTRUM FUeR INFEKTIONSFORSCHUNG GMBH; GOTTFRIED WILHELM LEIBNIZ UNIVERSITAeT HANNOVER; Baumann, Sascha; Herrmann, Jennifer; Mohr, Kathrin; Steinmetz, Heinrich; Gerth, Klaus; Raju, Ritesh; Mueller, Rolf; Hartmann, Rolf; Hamed, Mostafa; Elgaher, Walid A.M.; Moreno, Maria; Gille, Franziska; Wang, Liang Liang; Kirschning, Andreas; (196 pag.)US2016/145304; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics