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 65305

반응식

HRID 65305 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-441a4a04acb14102806f129ee8725680
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04613606

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