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

HRID 396440ノート

反応式

HRID 396440 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1469b72e87454828986792c16c35004c
出典データセット
uspto-grants-2003_08
特許番号
US06608070B1

反応ノート

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