Acetic Anhydride → Methyl 2-acetamido-4,5-dimethoxybenzoate

HRID 455872Notes

Reaction equation

HRID 455872 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[NH2:14].[C:16](OC(=O)C)(=[O:18])[CH3:17]>CCCCCCC>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[NH:14][C:16](=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 611144Methyl 4,5-dimethoxyanthranilate

Product 1

HCID 717609Methyl 2-acetamido-4,5-dimethoxybenzoate

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Commercially available 2-amino-4,5-dimethoxy-benzoic acid methyl ester (3 g, 0.014 mol) and acetic anhydride (4.03 mL, 0.0426 mol) were heated in heptane at 100° C. for 3 hours. After removal of heptane in vaccuo, the crude product of 2-acetylamino-4,5-dimethoxy-benzoic acid methyl ester was obtained and used without further purification. LC/MS: m/z 254 (M+H).

Workup

  1. customAfter removal of heptane in vaccuo

Sources & evidence

ORD record
ord-78a1e21916024fa7ad90f62e826a0a83
Source dataset
uspto-grants-2013_07
Patent number
US08497284B2

Reaction notes

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