Formic Acid → HCID 178497005, 화합물

HRID 217001노트

반응식

HRID 217001 반응식
[CH3:1][O:2][C:3](=[O:23])[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][C:17]=1[CH3:22].[CH:24](O)=O>CCO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]([C:4]1[C:5]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[C:6]([F:14])[C:7]2[NH:13][CH:24]=[N:10][C:8]=2[CH:9]=1)=[O:23]

참가 물질

5

반응물 2

HCID 284Formic Acid2회HCID 22180129Methyl 4-amino-3-fluoro-5-nitro-2-(2-toluidino)benzoate

생성물 1

HCID 178497005HCID 178497005, 화합물

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매2회HCID 702Ethanol용매

반응 조건

온도
95 °C

실험 절차

4-Amino-3-fluoro-5-nitro-2-o-tolylamino-benzoic acid methyl ester 5a (1.57 g, 4.92 mmol), formic acid (25 mL, 26.5 mmol) and 20% Pd(OH)2/C (1.57 g, 2.95 mmol) in 25 mL EtOH are heating with stirring to 95° C. After 16 hours, the reaction mixture is cooled to room temperature and 0.5 g 20% Pd(OH)2/C and 10 mL formic acid added. The reaction mixture is heated to 95° C. with stirring. After 16 hours, the reaction mixture is cooled to room temperature and filtered through Celite rinsing with EtOH. The filtrate is concentrated under reduced pressure until the desired product precipitates. The desired product is collected by filtration. The filtrate is concentrated again until more desired product precipitates. The product is collected by filtration. Repeated EtOH concentration, product filtration several times. Recovered 1.09 g (74%) pure desired product: MS APCI (+) m/z 300 (M+1) detected; MS APCI (−) m/z 298 (M−1) detected.

후처리

  1. temperaturethe reaction mixture is cooled to room temperature
  2. temperatureThe reaction mixture is heated to 95° C.
  3. stirringwith stirring
  4. waitAfter 16 hours
  5. temperaturethe reaction mixture is cooled to room temperature
  6. filtrationfiltered through Celite
  7. washrinsing with EtOH
  8. concentrationThe filtrate is concentrated under reduced pressure until the desired product
  9. customprecipitates
  10. filtrationThe desired product is collected by filtration
  11. concentrationThe filtrate is concentrated again until more desired product
  12. customprecipitates
  13. filtrationThe product is collected by filtration
  14. concentrationRepeated EtOH concentration, product filtration several times
  15. customRecovered 1.09 g (74%) pure desired product

출처 및 근거

ORD 기록
ord-ed7166b8b78a4dafbdd55bc0c74f8e57
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193231B2

반응 노트

불러오는 중…