Dimethylacetamide → Quinoline

HRID 982196

Reaction equation

HRID 982196 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=O)OC(=O)[C:5]2=[CH:11][C:12]=1F.[F:14][C:15]1[CH:16]=[C:17]([C:25]([OH:27])=[O:26])[C:18](=[CH:22][C:23]=1[F:24])C(O)=O.[CH3:28][C:29]([N:31](C)C)=O>CN1CCCC1=O>[N:31]1[C:5]2[C:4](=[CH:3][CH:2]=[CH:12][CH:11]=2)[CH:9]=[CH:28][CH:29]=1.[F:14][C:15]1[CH:16]=[C:17]([CH:18]=[CH:22][C:23]=1[F:24])[C:25]([OH:27])=[O:26]

Participants

6

Reactant 3

HCID 31374DimethylacetamideHCID 6397454,5-Difluorophthalic AnhydrideHCID 6433824,5-Difluorophthalic Acid

Product 2

HCID 7047QuinolineHCID 991663,4-Difluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Surprisingly, we have found that 4,5-difluorophthalic anhydride and 4,5-difluorophthalic acid may be selectively decarboxylated in N-methyl-pyrrolidone, dimethyl acetamide or quinoline to yield 3,4-difluorobenzoic acid.

Sources & evidence

ORD record
ord-d666b3202b4042d58b36b042b1da0a9d
Source dataset
uspto-grants-1991_02
Patent number
US04994606

Linked notes

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