Sodium Hydroxide → N-[3-(2-Hydroxyethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide

HRID 1107953Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

N-[1-Acetyl-3-(2-acetoxyethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide (4.0 g) was dissolved in EtOH (40 ml) and a solution of NaOH (2.2 g) in water (10 ml) was added, which was followed by stirring at 60° C. for 10 hr. EtOH was evaporated under reduced pressure, and CHCl3 (100 ml) was added. After washing with water, the mixture was dried over anhydrous sodium sulfate, and CHCl3 was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1) to give 1.6 g of N-[3-(2-hydroxyethyl)-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide.

Workup

customEtOH was evaporated under reduced pressure, and CHCl3 (100 ml)
additionwas added
washAfter washing with water
dry with materialthe mixture was dried over anhydrous sodium sulfate, and CHCl3
customwas evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1)

Sources & evidence

ORD record: ord-0d0811f08f2b41d2a57dc51419f94ed6
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06063806

Reaction notes

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