Acetyl chloride → N-(3,4-Dimethoxy-6-methylphenanthren-9-yl)acetamide

HRID 746003Notes

Reaction equation

HRID 746003 reaction equation
C(N(C(C)C)C(C)C)C.[NH2:10][C:11]1[C:12]2[C:17]([C:18]3[C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][C:23]=3[CH:24]=1)=[CH:16][C:15]([CH3:29])=[CH:14][CH:13]=2.[C:30](Cl)(=[O:32])[CH3:31]>C(Cl)Cl>[C:30]([NH:10][C:11]1[C:12]2[C:17]([C:18]3[C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][C:23]=3[CH:24]=1)=[CH:16][C:15]([CH3:29])=[CH:14][CH:13]=2)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 137729823,4-Dimethoxy-6-methylphenanthren-9-amine

Product 1

HCID 13772983N-(3,4-Dimethoxy-6-methylphenanthren-9-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

105.7 ml (0.750M) of N-ethyl-N,N-diisopropyl-amine are added to a solution of 100.2 g (0.375M) of 9-amino-3,4-dimethoxy-6-methyl-phenanthrene in 1000 ml methylene chloride. To the resulting mixture is added dropwise over 30 minutes a solution of 34.5 ml (0.450M) of acetyl chloride in 250 ml methylene chloride. During the addition, the temperature of the reaction mixture is maintained at 20° by cooling with ice. The reaction mixture is stirred for 2 hours at room temperature and extracted with methylene chloride. The organic phases are washed with ice cooled 2N hydrochloric acid, water and 2N sodium bicarbonate, dried over sodium sulfate and evaporated, to give the title compound. M.pt. 190°-192° after crystallization from acetone/ether.

Workup

  1. additionDuring the addition
  2. temperaturethe temperature of the reaction mixture is maintained at 20°
  3. temperatureby cooling with ice
  4. extractionextracted with methylene chloride
  5. washThe organic phases are washed with ice
  6. temperaturecooled 2N hydrochloric acid, water and 2N sodium bicarbonate
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-f7719ade5240409bbef9d8b9598211f3
Source dataset
uspto-grants-1986_07
Patent number
US04602032

Reaction notes

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