Dimethylformamide → (E)-2-(2-chloro-5-nitropyridin-4-yl)-N,N-diMethylethenaMine

HRID 1028041Notes

Reaction equation

HRID 1028041 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][N:13]([CH3:16])[CH:14]=O>>[Cl:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:12]/[N:13]([CH3:16])[CH3:14])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 3453642-Chloro-4-methyl-5-nitropyridine

Product 1

HCID 6163756(E)-2-(2-chloro-5-nitropyridin-4-yl)-N,N-diMethylethenaMineYield 70%

Procedure

A solution of 2-chloro-4-methyl-5-nitropyridine (1.0 equiv), 25.2 mL dimethylacetal dimethylformamide (2.2 equiv.) in dimethylformamide (0.8 M) was heated at 95° C. for 18 hours. Upon cooling the volatiles were removed in vacuo. The crude material was recrystallized from boiling methanol to yield (E)-2-(2-chloro-5-nitropyridin-4-yl)-N,N-dimethylethenamine (70%) as a red solid. 1H NMR (CDCl3): δ 8.80 (s, 1H), 7.32 (d, J=13.2, 1H), 7.25 (s, 1H), 5.95 (d, J=13.2, 1H), 3.02 (bs, 6H).

Workup

  1. temperatureUpon cooling the volatiles
  2. customwere removed in vacuo
  3. customThe crude material was recrystallized

Sources & evidence

ORD record
ord-ffd0d0c6c500477e9f5ef842808054f7
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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