Hydrochloric Acid → HCID 13882041, compound

HRID 231060Notes

Reaction equation

HRID 231060 reaction equation
C([O:4][C:5]1[C:6]([O:23][CH3:24])=[CH:7][C:8]2[N:9]([CH3:22])[C:10]3[C:15]([S:16][C:17]=2[C:18]=1[Br:19])=[CH:14][C:13]([O:20][CH3:21])=[CH:12][CH:11]=3)(=O)C.[OH-].[Na+].Cl>CO>[Br:19][C:18]1[C:17]2[S:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:20][CH3:21])[CH:14]=3)[N:9]([CH3:22])[C:8]=2[CH:7]=[C:6]([O:23][CH3:24])[C:5]=1[OH:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13882040HCID 13882040, compound

Product 1

HCID 13882041HCID 13882041, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3-acetoxy-4-bromo-2,7-dimethoxy-10-methyl-10H-phenothiazine (0.5 g) in methanol (300 ml) there was added 2N aqueous sodium hydroxide (300 ml) and the mixture was stirred at room temperature overnight. The heterogenous mixture was then acidified with 1N aqueous HCl solution, and after stirring for 15 minutes the product filtered. This crude product was purified by flash chromatography on a column of silica gel, eluting with a 1:1 mixture of ethyl acetate and hexane, and the pure title product (211 mg) was obtained. m.p. 154°-155° C.

Workup

  1. stirringafter stirring for 15 minutes the product
  2. filtrationfiltered
  3. customThis crude product was purified by flash chromatography on a column of silica gel
  4. washeluting with a 1:1 mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-3fdfe3b77b8146ecba73f70b82061438
Source dataset
uspto-grants-1989_07
Patent number
US04845083

Reaction notes

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