Acetic Anhydride → 2-Acetylamino-3,4,5,6-tetrafluorobenzoic acid

HRID 979466Notes

Reaction equation

HRID 979466 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH2:14].[C:15](OC(=O)C)(=[O:17])[CH3:16]>C(O)(=O)C>[C:15]([NH:14][C:3]1[C:2]([F:1])=[C:10]([F:11])[C:9]([F:12])=[C:8]([F:13])[C:4]=1[C:5]([OH:7])=[O:6])(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 6881852-Amino-3,4,5,6-tetrafluorobenzoic acid

Product 1

HCID 199057552-Acetylamino-3,4,5,6-tetrafluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compounds of the Formula II may be prepared by a series of reactions starting with 3,4,5,6-tetrafluoroanthranilic acid. The acid is reacted with acetic anhydride and acetic acid to form 2-acetylamino-3,4,5,6-tetrafluorobenzoic acid. This compound is reacted with oxalyl chloride and dichloromethane in the presence of N,N-dimethylformamide catalyst to form 2-acetylamino-3,4,5,6-tetrafluorobenzoyl chloride. This product is treated with n-butyl lithium and malonic half acid ester to form 2-acetylamino-3,4,5,6-tetrafluoro-β-oxobenzene-propanoic acid ethyl ester.

Sources & evidence

ORD record
ord-80ff181c3ef54011a0ba8b7ef52150b3
Source dataset
uspto-grants-1987_05
Patent number
US04668680

Reaction notes

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