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]2Participants
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
- temperaturethe reaction mixture was cooled to room temperature
- customThe aqueous phase was separated
- extractionextracted with two 250 ml-portions of dichloromethane
- temperatureThe aqueous phase was then cooled in an ice-bath
- extractionThe product was extracted out with three 500 ml-portions of dichloromethane
- washThe combined organic extracts were washed twice with brine
- customdried
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c00a9480d9f0457d8175dcbd5a9b8e1d
- Source dataset
- uspto-grants-1988_02
- Patent number
- US04723007
Linked notes
Loading…