Hydrochloric Acid → Benzyl 4-[3-(3-nitrobenzyl)indol-1-yl]-4-oxobutyrate

HRID 249155Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[C:22]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=[O:34])[CH2:23][CH2:24][C:25](OC1C=CC=CC=1)=[O:26].Cl>CN(C)C=O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:25](=[O:26])[CH2:24][CH2:23][C:22]([O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:34])[CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-(3-nitrobenzyl)indole (280 mg) in N,N-dimethylformamide (5 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 66.6 mg) in N,N-dimethylformamide (10 ml) at 0° C. The mixture was stirred at 25° C. for 40 minutes, and a solution of benzyl phenyl succinate (316 mg) in N,N-dimethylformamide was added at -40° C. After stirred at -40° C. for 20 minutes, the reaction mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over, magnesium sulfate. After evaporation of the solvent, the crude crystals were washed with hot isopropyl ether to give benzyl 4-[3-(3-nitrobenzyl)indol-1-yl]-4-oxobutyrate (364 mg).

Workup

stirringAfter stirred at -40° C. for 20 minutes
customThe organic layer was separated
washwashed with water and brine
dry with materialdried over, magnesium sulfate
customAfter evaporation of the solvent
washthe crude crystals were washed with hot isopropyl ether

Sources & evidence

ORD record: ord-f987f97db3f54769b1057ea5e79dfa11
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05212320

Reaction notes

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