Sodium Hydroxide → 10-Nitro-7H-benzo[c]phenothiazine-8-carboxylic acid

HRID 617808Notes

Reaction equation

HRID 617808 reaction equation
[OH-].[Na+].[NH2:3][CH:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[S:14].Cl[C:16]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][C:23]([N+]([O-])=O)=[CH:22][C:17]=1[C:18]([O:20]C)=[O:19]>C(O)C>[N+:26]([C:25]1[CH:24]=[C:23]2[C:22](=[C:17]([C:18]([OH:20])=[O:19])[CH:16]=1)[NH:3][C:4]1[CH:13]=[CH:12][C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]=1[S:14]2)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 248909methyl 2-chloro-3,5-dinitrobenzoateHCID 218499792-Amino-1-naphthalenethione

Product 1

HCID 2184996110-Nitro-7H-benzo[c]phenothiazine-8-carboxylic acidYield 34.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

5 ml of a 2 N aqueous solution of sodium hydroxide was added to a solution of 1.7 g (9.73 mmol) of 2-amino-1-naphthalenethione in ethanol (30 ml) and the obtained mixture was heated under reflux. To this mixture was added 2.54 g(9.76 mmol) of methyl 2-chloro-3,5-dinitrobenzoate and the obtained mixture was heated under reflux for 1 hour. To this mixture were added 10 ml of a 2 N aqueous solution of sodium hydroxide and 40 ml of ethanol and the obtained mixture was heated under reflux for additional 10 hours. Then it was brought back to room temperature and concentrated. After adding water, 1 N hydrochloric acid was slowly added thereto under stirring to thereby regulate the pH value to about 1. The precipitate was recovered by filtration and washed successively with ethanol and methanol to thereby give 1.14 g of the title compound.

Workup

  1. temperaturethe obtained mixture was heated
  2. temperatureunder reflux
  3. temperaturethe obtained mixture was heated
  4. temperatureunder reflux for 1 hour
  5. temperaturethe obtained mixture was heated
  6. temperatureunder reflux for additional 10 hours
  7. customwas brought back to room temperature
  8. concentrationconcentrated
  9. additionAfter adding water, 1 N hydrochloric acid
  10. additionwas slowly added
  11. filtrationThe precipitate was recovered by filtration
  12. washwashed successively with ethanol and methanol

Sources & evidence

ORD record
ord-e02ef8d7ec0f4dc59b87f06476f89f00
Source dataset
uspto-grants-1999_09
Patent number
US05952335

Reaction notes

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