5-nitro-1-(2-pyrrolidin-1-ylethyl)-1H-indole → 5-Amino-1-(2-pyrrolidin-1-ylethyl)indole

HRID 1820866Notes

Reaction equation

HRID 1820866 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[CH:8]=[CH:7]2)([O-])=O.ClCCl.CO.N>C1COCC1>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 114026955-nitro-1-(2-pyrrolidin-1-ylethyl)-1H-indoleHCID 21584172Ammonia methanol dichloromethane

Product 1

HCID 113905745-Amino-1-(2-pyrrolidin-1-ylethyl)indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example VI.1.d from 27.0 g (104 mmol) of 5-nitro-1-(2-pyrrolidin-1-ylethyl)-1H-indole (VII.1.a) in THF as solvent. Yield: 23.2 g (97% of theory); Rf value: 0.50 (silica gel, dichloromethane/methanol/ammonia=9:1:0.1); C14H19N3; EII mass spectrum: m/z=230 [M+H]+.

Sources & evidence

ORD record
ord-e319f9a028514cdda97f91829d9464c9
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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