Methyl propiolate → 6-Hydroxy-2-methylnicotinonitrile

HRID 241687ノート

反応式

HRID 241687 の反応式
[NH2:1]/[C:2](/[CH3:6])=[CH:3]/[C:4]#[N:5].C[O:8][C:9](=O)[C:10]#[CH:11].C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>CN(C=O)C>[CH3:6][C:2]1[NH:1][C:9](=[O:8])[CH:10]=[CH:11][C:3]=1[C:4]#[N:5]

参加物

5

反応物 3

HCID 13536Methyl propiolateHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 53247203-Aminocrotonitrile

生成物 1

HCID 113785166-Hydroxy-2-methylnicotinonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
230 °C

実験手順

A solution of (E)-3-amino-but-2-enenitrile (100 g) and propynoic acid methyl ester in DMF (200 ml) was stirred at 25° C. for 2 h and refluxed for additional 1 h. Dowtherm (100 ml) was added and the temperature was raised to 230° C. DMF and MeOH were distilled off. The reaction mixture was cooled down, EtOAc (200 ml) was added and the resulting crystals were filtered off and washed with EtOAc and ether affording the title compound (44.8 g, FP>250° C.).

後処理

  1. temperaturerefluxed for additional 1 h
  2. distillationDMF and MeOH were distilled off
  3. temperatureThe reaction mixture was cooled down
  4. additionEtOAc (200 ml) was added
  5. filtrationthe resulting crystals were filtered off
  6. washwashed with EtOAc and ether affording the title compound (44.8 g, FP>250° C.)

出典と根拠

ORDレコード
ord-61b9afaa144d4e7699a02c1b23f562a5
出典データセット
uspto-grants-2014_02
特許番号
US08653075B2

反応ノート

読み込み中…