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

HRID 563041Notes

Reaction equation

HRID 563041 reaction equation
FC1C=CC(N[C:9]([C:11]2(C(NC3C=CC(OC4C5C(=CC(OC)=C(OC)C=5)N=C(C)N=4)=CC=3)=O)CC2)=[O:10])=CC=1.[CH3:39][O:40][C:41](=[O:53])[C:42]1[CH:47]=[C:46]([O:48][CH3:49])[C:45]([O:50][CH3:51])=[CH:44][C:43]=1[NH2:52].C(OC(=O)C)(=O)C>CCCCCCC>[CH3:39][O:40][C:41](=[O:53])[C:42]1[CH:47]=[C:46]([O:48][CH3:49])[C:45]([O:50][CH3:51])=[CH:44][C:43]=1[NH:52][C:9](=[O:10])[CH3:11]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 611144Methyl 4,5-dimethoxyanthranilateHCID 57810414N-(4-fluorophenyl)-N'-(4-{[2-methyl-6,7-bis(methyloxy)quinazolin-4-yl]oxy}phenyl)cyclopropane-1,1-dicarboxamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

′N-(4-fluorophenyl)-N′-(4-{[2-methyl-6,7-bis(methyloxy)quinazolin-4-yl]oxy}phenyl)cyclopropane-1,1-dicarboxamide. 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 vacuo, 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 vacuo

Sources & evidence

ORD record
ord-b5db8bea1efe41ea81cf10ccbf1b3050
Source dataset
uspto-grants-2011_11
Patent number
US08067436B2

Reaction notes

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