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

HRID 4023
Notes
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Reaction equation

HRID 4023 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
2×

Conditions

Temperature
175 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c00a9480d9f0457d8175dcbd5a9b8e1d
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04723007

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes