Triethylamine → N-(4-Methoxybenzyl)-2-bromo-5-nitropyridin-4-amine

HRID 40652ノート

反応式

HRID 40652 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:17]=[C:16](Cl)[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][N:13]=1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:16]2[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][N:13]=[C:12]([Br:11])[CH:17]=2)=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 596134182-Bromo-4-chloro-5-nitropyridine

生成物 1

HCID 56926468N-(4-Methoxybenzyl)-2-bromo-5-nitropyridin-4-amine収率 77.2%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 4-methoxybenzylamine (0.756 g, 5.51 mmol) in acetonitrile (2 mL) was added to a mixture of 2-bromo-4-chloro-5-nitropyridine (1.19 g, 5.01 mmol) and triethylamine (0.768 mL, 5.51 mmol) in acetonitrile (8 mL). After stirring for 1.5 hours, the solution was diluted with ethyl acetate (100 mL) which was then washed successively with water and brine before being concentrated in vacuo to a light brown oil which solidified on standing to give the title compound (1.31 g, 3.87 mmol, 77%). 1H NMR (d6-DMSO, 400 MHz) δ 9.00 (br t, 1H, J=6.3 Hz), 8.80 (s, 1H), 7.35 (d, 2H, J=8.7 Hz), 7.10 (s, 1H), 6.95 (d, 2H, J=8.8 Hz), 4.60 (d, 2H, J=6.0 Hz), 3.70 (s, 3H). LCMS (1) Rt=2.13 min; m/z (ESI−) 336, 338 (M−H).

後処理

  1. washwas then washed successively with water and brine
  2. concentrationbefore being concentrated in vacuo to a light brown oil which

出典と根拠

ORDレコード
ord-2e3d4c2515ea484f98336fd06b5114a8
出典データセット
uspto-grants-2013_09
特許番号
US08530468B2

反応ノート

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