Dimethylformamide → [2-(2-Chloro-5-nitro-pyridin-4-yl)-vinyl]dimethyl-amine

HRID 1370043Notes

Reaction equation

HRID 1370043 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]([CH:15]=O)[CH3:14]>>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH:12][N:13]([CH3:15])[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 4611300[2-(2-Chloro-5-nitro-pyridin-4-yl)-vinyl]dimethyl-amineYield 90%

Conditions

Temperature
100 °C

Procedure

A solution of 2-chloro-4-methyl-5-nitro-pyridine (2 g, 11.59 mmol) in DMF (11.6 mL) was treated with 3.08 mL (23.2 mmol, 2 eq) of DMF-dimethylacetal and the reaction mixture was stirred at 100° C. for 4 h. All volatiles were removed under reduced pressure. Column chromatography (silica, 20% EtOAc/hexanes) provided 2.37 g (90%) of [2-(2-chloro-5-nitro-pyridin-4-yl)-vinyl]-dimethyl-amine. TLC (silica, 20% EtOAc/hexanes): Rf=0.30. MS (electrospray): exact mass calculated for C9H10ClN3O2, 227.05; m/z found, 228.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.79 (s, 1H), 8.02 (s, 1H), 7.35 (d, J=13 Hz, 1H), 5.94 (d, J=13 Hz, 1H), 2.96 (s, 3H), 2.87 (s, 3H).

Workup

  1. customAll volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-daf6e6fdde574a5f83b3f40d8ce7efec
Source dataset
uspto-grants-2003_06
Patent number
US06579896B2

Reaction notes

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