Cyanoacetamide → 6-[m-(4-Methyl-1-piperazinyl)phenyl]-1,2-dihydro-2-oxonicotinonitrile

HRID 972691

反応式

HRID 972691 の反応式
C[O-].[Na+].[CH3:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[C:13]([C:17](=O)[CH3:18])[CH:14]=[CH:15][CH:16]=2)[CH2:7][CH2:6]1.C(OCC)=O.C(CC(N)=O)#N.[O:31]=[C:32]1[NH:39]C=C[CH:36]=[C:33]1[C:34]#[N:35]>O.C(OCC)C>[CH3:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[C:13]([C:17]3[NH:39][C:32](=[O:31])[C:33](=[CH:36][CH:18]=3)[C:34]#[N:35])[CH:14]=[CH:15][CH:16]=2)[CH2:7][CH2:6]1

参加物

8

反応物 5

HCID 7898CyanoacetamideHCID 8025Ethyl formateHCID 5775433-Cyano-2-pyridoneHCID 108464921-[3-(4-Methyl-piperazin-1-YL)-phenyl]-ethanoneHCID 10942334Sodium Methoxide

生成物 1

HCID 214045966-[m-(4-Methyl-1-piperazinyl)phenyl]-1,2-dihydro-2-oxonicotinonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

A suspension of 5.3 g. (0.098 mole) of sodium methoxide in 100 ml. ethyl ether under nitrogen is cooled to 3° and treated dropwise with a solution of 18.4 g. (0.084 mole) of m-(4-methyl-1-piperazinyl)acetophenone and 6.25 g. (0.084 mole) of ethyl formate in 100 ml. ethyl ether while keeping the temperature below 5°. When the addition is completed, the mixture is allowed to stir at room temperature overnight. 100 ml. water is then added and the layers separated. The ethyl ether layer is washed with an additional 75 ml. water. The pH of the aqueous layer is adjusted to pH 9 with acetic acid. 10.6 g. (0.126 mole) of cyanoacetamide is then added and the solution heated at 90° for 6 hours. A solid formed which is collected and dried. Recrystallization from DMSO/water gives 14.8 g. (60.2%) of pure 6-m-(4-methyl-1-piperazinyl)-phenyl]-1,2-dihydro-2-oxonicotinonitrile, m.p. 264°-267° d., as a yellow solid.

後処理

  1. additionA suspension of 5.3 g
  2. additiontreated dropwise with a solution of 18.4 g
  3. customthe temperature below 5°
  4. additionWhen the addition
  5. customthe layers separated
  6. washThe ethyl ether layer is washed with an additional 75 ml
  7. temperaturethe solution heated at 90° for 6 hours
  8. customA solid formed which
  9. customis collected
  10. customdried
  11. customRecrystallization from DMSO/water
  12. customgives 14.8 g

出典と根拠

ORDレコード
ord-a29f3859630e45c6abecabc35359d74c
出典データセット
uspto-grants-1977_10
特許番号
US04053470

関連ノート

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