Methyl propiolate → 6-Hydroxy-2-methylnicotinonitrile

HRID 241687

반응식

HRID 241687 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 113785166-Hydroxy-2-methylnicotinonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
230 °C

실험 절차

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.).

후처리

  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.)

출처 및 근거

ORD 기록
ord-61b9afaa144d4e7699a02c1b23f562a5
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653075B2

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