Hydrochloric Acid → HCID 9840135, compound

HRID 617814Notes

Reaction equation

HRID 617814 reaction equation
[NH2:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl[C:14]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:21]([N+]([O-])=O)=[CH:20][C:15]=1[C:16]([O:18]C)=[O:17].C([O-])(=O)C.[Na+].[OH-].[Na+].Cl>O.C(O)C>[N+:24]([C:23]1[CH:22]=[C:21]2[C:20](=[C:15]([C:16]([OH:18])=[O:17])[CH:14]=1)[NH:1][C:2]1[CH:11]=[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]3=[CH:4][C:3]=1[O:12]2)([O-:26])=[O:25]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 794493-Amino-2-naphtholHCID 248909methyl 2-chloro-3,5-dinitrobenzoateHCID 517045Sodium Acetate

Product 1

HCID 9840135HCID 9840135, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

304 mg (1.91 mmol) of 3-amino-2-naphthol, 477 mg (1.81 mmol) of methyl 2-chloro-3,5-dinitrobenzoate and 178 mg (2.17 mmol) of sodium acetate were suspended in a mixture of water (5 ml) with ethanol (10 ml) and heated under reflux for 7 hours. After adding 3 ml of a 2 N aqueous solution of sodium hydroxide thereto, the reaction mixture was heated under reflux for additional 2.5 hours and then brought back to room temperature. After adding 10 ml of 1 N hydrochloric acid thereto, the precipitate thus formed was recovered by filtration and washed successively with water, 1 N hydrochloric acid and ethanol to thereby give 430 mg of 3-nitro-12H-benzo[b]phenoxazine-1-carboxylic acid. Then this product was treated by the same methods as those of Production Example 23 and Example 13 to thereby give the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 7 hours
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for additional 2.5 hours
  5. custombrought back to room temperature
  6. customthe precipitate thus formed
  7. filtrationwas recovered by filtration
  8. washwashed successively with water, 1 N hydrochloric acid and ethanol

Sources & evidence

ORD record
ord-0bd02a4b19d64b87b097d455194a448f
Source dataset
uspto-grants-1999_09
Patent number
US05952335

Reaction notes

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