Sodium Dithionite → 5-hydroxy-6-methyl-12H-benzo[a]phenothiazine

HRID 64966Notes

Reaction equation

HRID 64966 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH3:9][C:10]1[C:11](=[O:28])[C:12]2[CH:27]=[CH:26][CH:25]=[CH:24][C:13]=2[C:14]2[C:23]=1[S:22][C:21]1[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=1)[N:15]=2>O.C(OCC)(=O)C>[OH:28][C:11]1[C:10]([CH3:9])=[C:23]2[C:14]([NH:15][C:16]3[C:21]([S:22]2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:13]2[CH:24]=[CH:25][CH:26]=[CH:27][C:12]=12

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 2794416-Methyl-5H-benzo(a)phenothiazin-5-one

Product 1

HCID 146014105-hydroxy-6-methyl-12H-benzo[a]phenothiazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of sodium hydrosulfite (40 g) in water (0.5 l) was added to a suspension of 6-methyl-5H-benzo[a]phenothiazine-5-one (10.4 g) in ethyl acetate (1 l) and stirred for 2 hours. The organic layer was decanted, dried and evaporated to dryness. The resulting residue was triturated with ether and filtered to afford 5-hydroxy-6-methyl-12H-benzo[a]phenothiazine as an air sensitive solid.

Workup

  1. customThe organic layer was decanted
  2. customdried
  3. customevaporated to dryness
  4. customThe resulting residue was triturated with ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-265254cb448e42fdb63973d79a9202ea
Source dataset
uspto-grants-1986_09
Patent number
US04611056

Reaction notes

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