Acetic Anhydride → HCID 12805658, compound

HRID 1580599Notes

Reaction equation

HRID 1580599 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[C:9]([CH3:15])=[C:8]4[CH:16]=[CH:17][N:18]=[CH:19][C:7]4=[C:6]([CH3:20])[C:5]=3[C:4]=2[CH:3]=1.C([O-])(O)=O.[Na+].[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(Cl)(=O)C>[C:26]([O:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[C:9]([CH3:15])=[C:8]4[CH:16]=[CH:17][N:18]=[CH:19][C:7]4=[C:6]([CH3:20])[C:5]=3[C:4]=2[CH:3]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 916439-HydroxyellipticineHCID 516892Sodium Bicarbonate

Product 1

HCID 12805658HCID 12805658, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6367Acetyl chlorideSolvent

Procedure

A solution of 9-hydroxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole (10 g.) in acetic anhydride (75 ml.) and acetyl chloride (25 ml.) was stirred at room temperature for 2 hours. The reaction mixture was poured into excess NaHCO3 solution and stirred for 10 minutes. The resulting precipitate was removed by filtration and was washed well with water. The dried solids (10 g.; 86%) were dissolved in tetrahydrofuran and the solution was charcoaled. Crystallization from tetrahydrofuran-ethyl acetate mixture afforded 9-acetoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole (8.3 g.; 75%), m.p. 303°-304°.

Workup

  1. customThe resulting precipitate was removed by filtration
  2. washwas washed well with water
  3. dissolutionThe dried solids (10 g.; 86%) were dissolved in tetrahydrofuran
  4. customCrystallization from tetrahydrofuran-ethyl acetate mixture

Sources & evidence

ORD record
ord-b16a7d4cf6e34b2885eeb464865180a6
Source dataset
uspto-grants-1976_01
Patent number
US03933827

Reaction notes

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