Acetic Acid → 5-Hydroxy-12H-benzo[a]phenothiazine-7,7-dioxide

HRID 979314Notes

Reaction equation

HRID 979314 reaction equation
C([O:4][C:5]1[CH:18]=[C:17]2[C:8]([NH:9][C:10]3[C:15]([S:16]2(=[O:20])=[O:19])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]=12)(=O)C.[OH-].[Na+].C(O)(=O)C.O>CO>[OH:4][C:5]1[CH:18]=[C:17]2[C:8]([NH:9][C:10]3[C:15]([S:16]2(=[O:20])=[O:19])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]=12

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 13712482HCID 13712482, compound

Product 1

HCID 137124805-Hydroxy-12H-benzo[a]phenothiazine-7,7-dioxideYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5-acetoxy-12H-benzo[a]phenothiazine-7,7-dioxide (6.6 g) in methanol (200 ml), kept under a nitrogen atmosphere was added 2N aqueous sodium hydroxide solution (132 ml). The mixture was stirred at room temperature for 7 minutes, then there was added 10% acetic acid (200 ml) and water (300 ml). After 10 minutes of stirring the mixture was filtered to afford the title compound (5.68 g) as a pink solid. The solid was recrystallized from THF, m.p. 334° C. (dec).

Workup

  1. stirringAfter 10 minutes of stirring the mixture
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-a09c4edb838c43b1a019a32fd03574ca
Source dataset
uspto-grants-1987_05
Patent number
US04667032

Reaction notes

Loading…