Ethanol → [5-Chloro-2-(4-methylpyridine-2-carbonyl)-1H-indol-3-yl]acetic Acid

HRID 396440노트

반응식

HRID 396440 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-])=O)=[C:6]([CH:13]=1)/[CH:7]=[CH:8]/[C:9]([O:11]C)=[O:10].[Cl-].[NH4+:18].[CH2:19]([OH:21])[CH3:20]>[Fe].O>[Cl:1][C:2]1[CH:13]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:14][C:20]([C:19]([C:8]1[CH:7]=[C:6]([CH3:13])[CH:5]=[CH:4][N:18]=1)=[O:21])=[C:7]2[CH2:8][C:9]([OH:11])=[O:10]

참가 물질

6

반응물 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 23003335Methyl trans-5-chloro-2-nitrocinnamate

생성물 1

HCID 23003314[5-Chloro-2-(4-methylpyridine-2-carbonyl)-1H-indol-3-yl]acetic Acid수율 98%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

실험 절차

A mixture of methyl trans-5-chloro-2-nitrocinnamate (step 1, 3.00 g, 12.42 mmol), iron powder (3.65 g, 62.08 mmol), ammonium chloride (332 mg, 6.21 mmol), ethanol (60 ml) and water (10 ml) was heated at reflux temperature for 2 h. The mixture was cooled and filtered through a pad of Celite. The filtrate was concentrated. The residue was diluted with ethyl acetate (200 ml) and washed with water (100 ml×2). After drying (MgSO4), removal of solvent gave 2.57 g (98%) of the title compound as crystals.

후처리

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through a pad of Celite
  5. concentrationThe filtrate was concentrated
  6. additionThe residue was diluted with ethyl acetate (200 ml)
  7. washwashed with water (100 ml×2)
  8. customAfter drying
  9. custom(MgSO4), removal of solvent

출처 및 근거

ORD 기록
ord-1469b72e87454828986792c16c35004c
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608070B1

반응 노트

불러오는 중…