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

HRID 35127

반응식

HRID 35127 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
175 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ca263d7b81ca4beda3f0ccebf20713ef
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04764616

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