4-Formyl-1-methyl-1H-pyrrole-2-carbonitrile → 4-Aminomethyl-1-methylpyrrole-2-carbonitrile

HRID 1582931Notes

Reaction equation

HRID 1582931 reaction equation
C(C1N(C)C=C(C=O)C=1)#N.NCC1N(C)C(C#N)=CC=1.[N:21]([CH2:24][C:25]1[CH:26]=[C:27]([C:31]#[N:32])[N:28]([CH3:30])[CH:29]=1)=[N+]=[N-]>>[NH2:21][CH2:24][C:25]1[CH:26]=[C:27]([C:31]#[N:32])[N:28]([CH3:30])[CH:29]=1

Participants

4

Reactant 3

HCID 141738604-Formyl-1-methyl-1H-pyrrole-2-carbonitrileHCID 225600125-(Aminomethyl)-1-methyl-1H-pyrrole-2-carbonitrileHCID 227159934-(azidomethyl)-1-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 227159964-Aminomethyl-1-methylpyrrole-2-carbonitrile

Procedure

Starting from 5-Cyano-1-methylpyrrole-3-carbaldehyde; 4-aminomethyl-1-methylpyrrole-2-carbonitrile was synthesized analogously to the synthesis of 5-aminomethyl-1-methylpyrrole-2-carbonitrile. However, the 4-azidomethyl-1-methylpyrrole-2-carbonitrile was advantageously reduced in a Staudinger reaction (see S. Nagarajan et al. J. Org. Chem. 1987, 52, 5044-6).

Sources & evidence

ORD record
ord-5eca5078d26e4e588ad1fe1f3b2ff332
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

Loading…