1-(3,4-Dimethoxyphenyl)-2-nitro-6-cyano-6-(prop-2-yl)-6-(3,4-dimethoxyphenyl)hexane → 1-(3,4-Dimethoxyphenyl)-2-amino-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexane

HRID 2119074

反応式

HRID 2119074 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([N+:32]([O-])=O)[CH2:13][CH2:14][CH2:15][C:16]([C:30]#[N:31])([CH:27]([CH3:29])[CH3:28])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH2:32])[CH2:13][CH2:14][CH2:15][C:16]([C:30]#[N:31])([CH:27]([CH3:29])[CH3:28])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

3

反応物 1

HCID 137457561-(3,4-Dimethoxyphenyl)-2-nitro-6-cyano-6-(prop-2-yl)-6-(3,4-dimethoxyphenyl)hexane

生成物 1

HCID 137457571-(3,4-Dimethoxyphenyl)-2-amino-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexane収率 95%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 1-(3,4-dimethoxyphenyl)-2-nitro-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexane (10, 58.7 g, 0.125 mol) and methanol (950 mL) was added to a flask, and evacuated to remove oxygen. The catalyst, 5% Pd in carbon (50% water, 19 g, Engelhard Co.), was added under an N2 atmosphere. After stirring for 10 minutes at room temperature, solid HCO2NH4 (65 g, Aldrich) was added, and the resulting mixture stirred for 1 hour. The mixture was then slowly heated to 50° C. for 48 hours, then cooled to room temperature and filtered through Celite (50 g). The solids were washed with methanol (50 mL), the filtrates concentrated in vacuo, and the resulting solid dissolved in CH2Cl2. The solution was extracted with saturated aqueous NH4Cl (500 mL) and saturated aqueous NaHCO3 (300 mL), and the organic layer evaporated to yield 1-(3,4-dimethoxyphenyl)-2-amino-6-cyano- 6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexane (11, 52.3 g, MS m/e 440(M+)) as a pale yellow oil.

後処理

  1. additionwas added to a flask
  2. customevacuated
  3. customto remove oxygen
  4. additionThe catalyst, 5% Pd in carbon (50% water, 19 g, Engelhard Co.), was added under an N2 atmosphere
  5. additionsolid HCO2NH4 (65 g, Aldrich) was added
  6. stirringthe resulting mixture stirred for 1 hour
  7. temperatureThe mixture was then slowly heated to 50° C. for 48 hours
  8. temperaturecooled to room temperature
  9. filtrationfiltered through Celite (50 g)
  10. washThe solids were washed with methanol (50 mL)
  11. concentrationthe filtrates concentrated in vacuo
  12. dissolutionthe resulting solid dissolved in CH2Cl2
  13. extractionThe solution was extracted with saturated aqueous NH4Cl (500 mL) and saturated aqueous NaHCO3 (300 mL)
  14. customthe organic layer evaporated

出典と根拠

ORDレコード
ord-c3ed418a7cf942838dd98975c5dbf3c0
出典データセット
uspto-grants-1987_07
特許番号
US04681889

関連ノート

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