Methane → 2-(1H-indol-3-yl)-5,5-dimethylcyclohexane-1,3-dione

HRID 1162168Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 2-(1-acetyl-1H-indol-3-yl)-5,5-dimethylcyclohexane-1,3-dione of Example 1e (74.8 g, 0.25 mol) and methanol (30 mL), a solution of sodium hydroxide (30 g, 0.75 mol) in water (300 mL) was added at room temperature under stirring. The reaction mixture was heated at 60° C. for 2 h under stirring, and then activated charcoal (10 g) and water (300 mL) were added. The mixture was stirred for 10 min, charcoal was filtered off, and the filtrate was acidified with hydrochloric acid to pH 2. The solid product was filtered off, washed with water and dried to give 38.3 g (60%) of the colorless solid; m.p. 173° C.

Workup

stirringunder stirring
stirringThe mixture was stirred for 10 min
filtrationcharcoal was filtered off
filtrationThe solid product was filtered off
washwashed with water
customdried

Sources & evidence

ORD record: ord-b5adfcce7aa948ada1da7f230105934d
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820691B2

Reaction notes

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