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

HRID 1952860Notes

Reaction equation

HRID 1952860 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

4-Aminomethyl-1-methylpyrrole-2-carbonitrile was prepared starting from 5-cyano-1-methylpyrrole-3-carbaldehyde similar to the synthesis of 5-aminomethyl-1-methylpyrrole-2-carbonitrile. However, the 4-azidomethyl-1-methylpyrrole-2-carbonitrile was advantageously reduced by a Staudinger reaction (see, for example, S. Nagarajan et al., J. Org. Chem. 52 (1987) 5044-6).

Sources & evidence

ORD record
ord-0b7164282a294d7d8b8c4773345d21ac
Source dataset
uspto-grants-2000_09
Patent number
US06114358

Reaction notes

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