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

HRID 2118846노트

반응식

HRID 2118846 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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. customThe dried (mgSO4) organic fraction
  5. customwas evaporated
  6. customthe residue was purified by column chromatography over silica gel with dichloromethane elution

출처 및 근거

ORD 기록
ord-82f880d3f4924f5e825acdf7012347a7
출처 데이터셋
uspto-grants-1987_07
특허 번호
US04680400

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