Sodium Nitrate → 2-(4-Hydroxy-3,5-dimethylphenyl)-3-methyl-5-nitroindole

HRID 2309406Notes

Reaction equation

[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH3:18])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:4][C:3]=1[CH3:19].[N+:20]([O-])([O-:22])=[O:21].[Na+]>S(=O)(=O)(O)O>[OH:1][C:2]1[C:3]([CH3:19])=[CH:4][C:5]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH3:18])=[CH:15][C:14]([N+:20]([O-:22])=[O:21])=[CH:13][CH:12]=3)=[CH:6][C:7]=1[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

5.0 g of 2-(4-hydroxy-3,5-dimethylphenyl)-3-methylindole was added to 100 ml of concentrated sulfuric acid, and the mixture was stirred at 0° C. Then, a solution of 1.76 g of sodium nitrate in 50 ml of concentrated sulfuric acid was added dropwise, and the mixture was stirred for 15 minutes. The reaction mixture was poured into ice-water, and extracted with ether. The resulting crude product was purified by silica gel column chromatography. Recrystallization from ether-hexane gave 2-(4-hydroxy-3,5-dimethylphenyl)-3-methyl-5-nitroindole.

Workup

stirringthe mixture was stirred for 15 minutes
extractionextracted with ether
customThe resulting crude product was purified by silica gel column chromatography
customRecrystallization from ether-hexane

Sources & evidence

ORD record: ord-1c40ab20eb104fdbacf4f5cf38199637
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04695581

Reaction notes

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