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Ammonium formate → Methyl 4,5-diamino-3-fluoro-2-(phenylamino)benzoate

HRID 216591
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HRID 216591 반응식
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([NH2:13])=[C:6]([F:14])[C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:13])=[C:6]([F:14])[C:5]=1[NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
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참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 44122658Methyl 4-amino-3-fluoro-5-nitro-2-(phenylamino)benzoate

생성물 1

HCID 56604175Methyl 4,5-diamino-3-fluoro-2-(phenylamino)benzoate수율 93.3%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

반응 조건

온도
95 °C

실험 절차

4-Amino-3-fluoro-5-nitro-2-phenylamino-benzoic acid methyl ester 26a (11.44 g, 37.48 mmol) is suspended in ethanol (400 mL) and ammonium formate (11.80 g, 187.0 mmol) and 20% Pd(OH)2/C (10.00 g, 18.79 mmol) are added. The reaction mixture is stirred at 95° C. under N2 for 30 minutes. The reaction mixture is cooled to room temperature and then filtered through celite, rinsing with ethanol. The filtrate is concentrated under reduced pressure to give 9.63 g (93%) of the pure desired product as a purple/red solid. MS ESI (+) m/z 276 (M+1) detected.

후처리

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationfiltered through celite
  3. washrinsing with ethanol
  4. concentrationThe filtrate is concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-eba4bf0ae69d47939e206b468b132e35
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08193230B2

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