Sodium Hydroxide → N-Ethyl-3,4-dimethoxy-6-methylphenanthren-9-amine

HRID 746004Notes

Reaction equation

HRID 746004 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([NH:14][C:15]1[C:16]2[C:21]([C:22]3[C:23]([O:31][CH3:32])=[C:24]([O:29][CH3:30])[CH:25]=[CH:26][C:27]=3[CH:28]=1)=[CH:20][C:19]([CH3:33])=[CH:18][CH:17]=2)(=O)[CH3:12].[OH-].[Na+]>C1(C)C=CC=CC=1.O1CCCC1>[CH2:11]([NH:14][C:15]1[C:16]2[C:21]([C:22]3[C:23]([O:31][CH3:32])=[C:24]([O:29][CH3:30])[CH:25]=[CH:26][C:27]=3[CH:28]=1)=[CH:20][C:19]([CH3:33])=[CH:18][CH:17]=2)[CH3:12]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 13772983N-(3,4-Dimethoxy-6-methylphenanthren-9-yl)acetamideHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 13772984N-Ethyl-3,4-dimethoxy-6-methylphenanthren-9-amine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1700 ml (2.05M) of a 20% solution of diisobutylaluminium hydride in toluene are added at room temperature over a period of 45 minutes to a suspension of 105.7 g (0.342M) of 9-acetylamino-3,4-dimethoxy-6-methyl-phenanthrene in 1500 ml anhydrous tetrahydrofuran. The mixture is then warmed with stirring under a nitrogen atmosphere for 2 hours at 80°. The reaction mixture is then cooled at 0° and under nitrogen atmosphere and a mixture of 2500 ml 2N hydrochloric acid/ice, cooled at -10°, is added by portions at such a rate that the gas evolution is maintained. The acid solution is made alkaline to pH 10 by addition at 0° of 3 liters 2N sodium hydroxide and the mixture is extracted three times with methylene chloride/2-propanol 7:3. The organic phases are combined, washed, dried and evaporated to give the title compound. M.pt. 100°-102° after crystallisation from acetone/ether.

Workup

  1. temperatureThe mixture is then warmed
  2. temperatureThe reaction mixture is then cooled at 0° and under nitrogen atmosphere
  3. temperaturecooled at -10°
  4. additionis added by portions at such a rate that the gas evolution
  5. temperatureis maintained
  6. extractionthe mixture is extracted three times with methylene chloride/2-propanol 7:3
  7. washwashed
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-d2da77d527e64dd3838e88a445b821ce
Source dataset
uspto-grants-1986_07
Patent number
US04602032

Reaction notes

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