1,1-Dimethoxyethyl(dimethyl)amine → 4-(2-Oxopropyl)pyridine-3-carbonitrile

HRID 491550

反応式

HRID 491550 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]#[N:9].C[O:11][C:12](OC)(N(C)C)[CH3:13]>CN(C=O)C>[CH2:1]([C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]#[N:9])[C:12]([CH3:13])=[O:11]

参加物

4

反応物 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 2278064-Methyl-3-cyanopyridine

生成物 1

HCID 219197754-(2-Oxopropyl)pyridine-3-carbonitrile収率 69%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-methyl-3-cyanopyridine (4 g, 33.9 mmol) and N,N-dimethylacetamide dimethylacetal (5.4 g, 40.6 mmol) in dry DMF (20 ml) was stirred at 130° for 7 h. The volatiles were removed in vacuo to afford a dark oil which solidified on standing. This material was chromatographed (SiO2; 50% EtOAc/Hexane—100% EtOAc) affording the title compound as an off-yellow solid (3.73 g, 69%). δH (CDCl3) 8.87 (1H, s), 8.74 (1H, d, J 5.2 Hz), 7.28 (1H, d, J 5,2 Hz), 4.00 (2H, s) and 2.36 (3H, s); m/z (ES+, 70V) 161 (MH+).

後処理

  1. customThe volatiles were removed in vacuo
  2. customto afford a dark oil which
  3. customThis material was chromatographed (SiO2; 50% EtOAc/Hexane—100% EtOAc)

出典と根拠

ORDレコード
ord-723e890102d143da9e52bbf6d28febd7
出典データセット
uspto-grants-2009_05
特許番号
US07531549B2

関連ノート

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