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

Reaktionsgleichung

Reaktionsgleichung von HRID 65305
[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]

Komponenten

3

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-441a4a04acb14102806f129ee8725680
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04613606

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