Acetic Acid → HCID 13712506, compound

HRID 2352227Notes

Reaction equation

HRID 2352227 reaction equation
[C:1]([N:4]1[C:17]2[C:12](=[C:13]([O:26]C(=O)C)[C:14]([O:22]C(=O)C)=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[S:11][C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[CH3:2].[OH-].[Na+].C(O)(=O)C>CC(C)=O>[C:1]([N:4]1[C:17]2[C:12](=[C:13]([OH:26])[C:14]([OH:22])=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[S:11][C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 13712505HCID 13712505, compound

Product 1

HCID 13712506HCID 13712506, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 12-acetyl-5,6-diacetoxy-12H-benzo[a]phenothiazine (450 mg) in acetone (10 ml) there was added 2N aqueous sodium hydroxide solution (10 ml) and the resulting mixture was stirred at room temperature for 45 minutes. It was then made slightly acidic by the addition of 10% aqueous acetic acid solution and the insolubles filtered and washed with water. The solid was swished in ethyl acetate to afford pure title compound (100 mg), m.p. 258°-260° C.

Workup

  1. filtrationthe insolubles filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-afe00aaedbda4aa9bd0d2e6eff499329
Source dataset
uspto-grants-1989_10
Patent number
US04876246

Reaction notes

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