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

HRID 966114ノート

反応式

HRID 966114 の反応式
[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

参加物

3

反応物 2

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

生成物 1

HCID 4611300[2-(2-Chloro-5-nitro-pyridin-4-yl)-vinyl]dimethyl-amine収率 90%

反応条件

温度
100 °C

実験手順

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).

後処理

  1. customAll volatiles were removed under reduced pressure

出典と根拠

ORDレコード
ord-f263f51f78294c5281a215d0c38d4d1c
出典データセット
uspto-grants-2005_10
特許番号
US06951851B2

反応ノート

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