Dimethylformamide diethylacetal → N,N-Dimethyl-2-(3-nitropyridin-4-yl)ethenamine

HRID 129466Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C(O[CH:14](OCC)[N:15]([CH3:17])[CH3:16])C>>[CH3:14][N:15](/[CH:17]=[CH:1]/[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])[CH3:16]

Participants

Reactant 2

HCID 70913Dimethylformamide diethylacetal

HCID 5218284-Methyl-3-nitropyridine

Product 1

HCID 11063279N,N-Dimethyl-2-(3-nitropyridin-4-yl)ethenamine

Procedure

Commercially available 4-methyl-3-nitropyridine is condensed with N,N-dimethylformamide diethyl acetal to provide E-4-[2-(N,N-dimethylamino)-1-ethenyl]-3-nitropyridine, which is then subjected to catalytic hydrogenation to give 6-azaindole.

Sources & evidence

ORD record: ord-e0d7c6e2ad1f47c78b58f92fa658c027
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05468757

Reaction notes

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