Sodium Hydroxide → N-(5-dimethylaminomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

HRID 1531954Notes

Reaction equation

C([N:4]1[C:12]2[C:7](=[C:8]([CH3:25])[C:9]([CH2:21][N:22]([CH3:24])[CH3:23])=[C:10]([CH3:20])[C:11]=2[NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+]>CO.O>[CH3:23][N:22]([CH2:21][C:9]1[C:8]([CH3:25])=[C:7]2[C:12](=[C:11]([NH:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:17])[CH3:18])[C:10]=1[CH3:20])[NH:4][CH2:5][CH2:6]2)[CH3:24]

Participants

Conditions

Temperature: 60 °C

Procedure

N-(1-Acetyl-5-dimethylaminomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide (1.0 g) was dissolved in MeOH (10 ml) and a solution of NaOH (580 mg) in water (3 ml) was added, which was followed by stirring at 60° C. for 2 hr. MeOH was evaporated under reduced pressure and CHCl3 (100 ml) was added. The mixture was washed with saturated brine and dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure to give 700 mg of N-(5-dimethylaminomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide.

Workup

customMeOH was evaporated under reduced pressure and CHCl3 (100 ml)
additionwas added
washThe mixture was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customCHCl3 was evaporated under reduced pressure

Sources & evidence

ORD record: ord-3751c49b9e6f44acb7e7cb73f4b96791
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06200988B1

Reaction notes

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