Ethylene Glycol → 2-(5-Methyl-7-nitro-1-indolinyl)benzoic acid

HRID 35127ノート

反応式

HRID 35127 の反応式
[OH-:1].[K+].[CH3:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[N:9]([C:16]1C=[CH:22][CH:21]=[CH:20][C:17]=1C#N)[CH2:8][CH2:7]2.ClCCl.[CH2:27]([OH:30])[CH2:28]O>O>[CH3:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[N:9]([C:16]1[CH:17]=[CH:20][CH:21]=[CH:22][C:28]=1[C:27]([OH:30])=[O:1])[CH2:8][CH2:7]2

参加物

6

反応物 4

HCID 174Ethylene GlycolHCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 138233372-(5-Methyl-7-nitroindolin-1-yl)benzonitrile

生成物 1

HCID 140236802-(5-Methyl-7-nitro-1-indolinyl)benzoic acid収率 32%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
175 °C

実験手順

A stirred solution under nitrogen of potassium hydroxide (30 g, 0.53 mole) in ethylene glycol (250 ml) and water (35 ml) was heated to 175° C., at which temperature there was added 2-(5-methyl-7-nitroindolin-1-Yl)benzonitrile (26 g, 0.093 mole). After heating at 175° C. for 3 hours, the reaction mixture was cooled to room temperature and dichloromethane (1 liter) and water (500 ml), were added, with stirring. The aqueous phase was separated and extracted with two 250 ml-portions of dichloromethane. The aqueous phase was then cooled in an ice-bath and acidified with concentrated hydrochloric acid. The product was extracted out with three 500 ml-portions of dichloromethane. The combined organic extracts were washed twice with brine, dried, filtered, and concentrated to afford 9.0 g (32%) of product.

後処理

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customThe aqueous phase was separated
  3. extractionextracted with two 250 ml-portions of dichloromethane
  4. temperatureThe aqueous phase was then cooled in an ice-bath
  5. extractionThe product was extracted out with three 500 ml-portions of dichloromethane
  6. washThe combined organic extracts were washed twice with brine
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-ca263d7b81ca4beda3f0ccebf20713ef
出典データセット
uspto-grants-1988_08
特許番号
US04764616

反応ノート

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