Acetic Anhydride → N-[(9,10-Methanoanthracen-9(10H)-yl)methyl]acetamide

HRID 27960Notes

Reaction equation

HRID 27960 reaction equation
[NH2:1][CH2:2][C:3]12[CH2:17][CH:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=31)[C:9]1[C:4]2=[CH:5][CH:6]=[CH:7][CH:8]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>C(O)C.O>[C:18]([NH:1][CH2:2][C:3]12[CH2:17][CH:10]([C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=31)[C:11]1[C:16]2=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 10900179HCID 10900179, compound

Product 1

HCID 13069084N-[(9,10-Methanoanthracen-9(10H)-yl)methyl]acetamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 9-aminomethyl-9,10-dihydro-9,10-methanoanthracene (235 mg) and acetic anhydride (217 mg) in ethanol (5.0 ml) was refluxed for 3 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate extract was washed with water, aqueous sodium bicarbonate and water, dried over anhydrous sodium sulfate and evaporated to dryness to give 9-acetylaminomethyl-9,10-dihydro-9,10-methanoanthracene. M.P. 184°-185.5° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water, aqueous sodium bicarbonate and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-08388479e296476fbe98a8096cfa9683
Source dataset
uspto-grants-1980_09
Patent number
US04224344

Reaction notes

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