Acetic Acid → 3-Chloro-1-phenylisoquinoline-4-carbaldehyde

HRID 443546ノート

反応式

HRID 443546 の反応式
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[N:13]=[C:14]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:15]2[C:20]([C:21]=1[C:22]#N)=[CH:19][CH:18]=[CH:17][CH:16]=2.C(O)(=[O:32])C.O>C1(C)C=CC=CC=1>[Cl:11][C:12]1[N:13]=[C:14]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:15]2[C:20]([C:21]=1[CH:22]=[O:32])=[CH:19][CH:18]=[CH:17][CH:16]=2

参加物

6

反応物 4

HCID 176Acetic AcidHCID 962WaterHCID 14567253HCID 14567253、化合物HCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 145672483-Chloro-1-phenylisoquinoline-4-carbaldehyde

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
0 °C

実験手順

In an atmosphere of argon and at -5° C. 10.7 ml of a 20% diisobutylaluminum hydride solution in toluene are slowly added dropwise to 2.64 g of 3-chloro-4-cyano-1-phenyl-isoquinoline in 150 ml of absolute toluene. The mixture is stirred for 10 minutes at 0° C. and then hydrolized with a small amount of glacial acetic acid until the reaction is weakly acid. Next, water is added and the toluene phase is separated. The organic phase is washed successively with saturated sodium bicarbonate solution and with water, dried and the solvent is removed under reduced pressure. The residue is rubbed with ether and recrystallized from ethyl acetate.

後処理

  1. customat -5° C
  2. customthe toluene phase is separated
  3. washThe organic phase is washed successively with saturated sodium bicarbonate solution and with water
  4. customdried
  5. customthe solvent is removed under reduced pressure
  6. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-37eb4c15d3c345d0ab3b70f99e69a031
出典データセット
uspto-grants-1981_04
特許番号
US04260763

反応ノート

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