Dimethylformamide → 4-Cyano-3-methoxy-1-methyl-5,6,7,8-tetrahydroisoquinoline

HRID 235588ノート

反応式

HRID 235588 の反応式
Cl[C:2]1[N:3]=[C:4]([CH3:14])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[C:12]#[N:13].C[O-].[Na+].CN(C)[CH:20]=[O:21]>CO>[C:12]([C:11]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4]([CH3:14])=[N:3][C:2]=1[O:21][CH3:20])#[N:13]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 37301863-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitrileHCID 10942334Sodium Methoxide

生成物 1

HCID 132957574-Cyano-3-methoxy-1-methyl-5,6,7,8-tetrahydroisoquinoline

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

3-Chloro-4-cyano-1-methyl-5,6,7,8-tetrahydroisoquinoline (10.0 g) was refluxed with sodium methoxide (1.1 equiv) in a mixture of methanol (150 ml) and anhydrous dimethylformamide (20 ml) for 24 hr. The bulk of the solvent was evaporated under reduced pressure, water was added to the residue and the resulting mixture was extracted with ether. The dried (MgSO4) organic fraction was evaporated and the residue was purified by column chromatography over silica gel with dichloromethane elution to give 4-cyano-3-methoxy-1-methyl-5,6,7,8-tetrahydroisoquinoline as white crystals, mp 116° C. Pmr spectrum (CDCl3 ; δ in ppm): 1.81 (4H,m); 2.39 (3H,s); 2.50-2.94 (4H,m); 3.98 (3H, s).

後処理

  1. customThe bulk of the solvent was evaporated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe resulting mixture was extracted with ether
  4. dry with materialThe dried (MgSO4) organic fraction
  5. customwas evaporated
  6. customthe residue was purified by column chromatography over silica gel with dichloromethane elution

出典と根拠

ORDレコード
ord-dc3f272c01c946c7b0f151d5dd8c51d6
出典データセット
uspto-grants-1987_02
特許番号
US04640708

反応ノート

読み込み中…