Trifluoroacetic acid → Ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-methoxynicotinoyl]acetate

HRID 246940Notes

Reaction equation

HRID 246940 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:39]=[C:38]([O:40][CH3:41])[C:37]([F:42])=[CH:36][C:11]=1[C:12]([CH:14](C(OCC)=O)[C:15]([O:17][CH:18](C1C=CC=CC=1)[C:19]1C=CC=CC=1)=[O:16])=[O:13].FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C1(OC)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:39]=[C:38]([O:40][CH3:41])[C:37]([F:42])=[CH:36][C:11]=1[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 13987861Diphenylmethyl ethyl 2-(2,4-difluorophenylamino)-5-fluoro-6-methoxynicotinoylmalonate

Product 1

HCID 15596920Ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-methoxynicotinoyl]acetateYield 94.3%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

In 2 ml of anisole was dissolved 200 mg of diphenylmethyl ethyl 2-(2,4-difluorophenylamino)-5-fluoro-6-methoxynicotinoylmalonate, and 2 ml of trifluoroacetic acid was added thereto with ice-cooling, after which the resulting mixture was subjected to reaction at the same temperature for 10 minutes. The solvent was removed by distillation under reduced pressure, and to the crystalline material thus obtained was added 2 ml of diisopropyl ether, after which crystals were collected by filtration to obtain 120 mg (yield 94.3%) of ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-methoxynicotinoyl]acetate.

Workup

  1. additionwas added
  2. temperaturewith ice-cooling
  3. customafter which the resulting mixture was subjected to reaction at the same temperature for 10 minutes
  4. customThe solvent was removed by distillation under reduced pressure
  5. customto the crystalline material thus obtained
  6. filtrationafter which crystals were collected by filtration

Sources & evidence

ORD record
ord-aa729a7752fe48f09cbed32d00827b95
Source dataset
uspto-grants-1987_11
Patent number
US04704459

Reaction notes

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