Hydrochloric Acid → 4-Amino-3-(4-methoxybenzamido)benzoic acid

HRID 252821Notes

Reaction equation

HRID 252821 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[NH:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.[OH-].[Na+].C1COCC1.Cl>CO>[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[NH:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 10732961Methyl 4-amino-3-(4-methoxybenzamido)benzoate

Product 1

HCID 597368674-Amino-3-(4-methoxybenzamido)benzoic acidYield 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 107 (400 mg, 1.33 mmol) and 1M NaOH (2.7 ml, 2.66 mmol) in 1:1 THF:MeOH (6 ml) was heated at 50° C. for 16 h. HCl 1M was added to reach pH=4 and the solid was filtered to give 370 mg (97%) of compound 108 as a white solid. 1H NMR: (DMSO) δ (ppm): 9.52 (s, 1H), 7.96 (d, J=8.8 Hz, 2H), 7.71 (d, J=2.0 Hz, 1H), 7.54 (dd, J=8.4, 2.0 Hz, 1H), 7.02 (d, J=9.0 Hz, 2H), 6.74 (d, J=8.4 Hz, 1H), 5.69 (s, 2H), 3.83 (s, 3H). MS: (calc.) 361.1; (obt.) 362.3 (MH)+.

Workup

  1. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-0b24b3463b0e43d08e3e14880d051b50
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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