Sulfuric Acid → HCID 21440157, compound

HRID 328933Notes

Reaction equation

HRID 328933 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:19]([O-:21])=[O:20])[C:10]=1[C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)[OH:23].N([O-])=O.[Na+]>O>[C:11]([C:10]1[C:9]([N+:19]([O-:21])=[O:20])=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[OH:23])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 12408770HCID 12408770, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21440157HCID 21440157, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 3-amino-4-benzoyl-5--nitrobenzoic acid (100 g) in a mixture of conc. sulfuric acid (875 ml) and water (280 ml) is dropwise added a solution of sodium nitrite (45.0 g) in water (280 ml), while stirring at -5° C to 0° C. After additional stirring at -5° C to 0° C for about 15 minutes, the resulting diazoniumsolution is heated on a steam bath for 2-3 hours until the nitrogen evolution has ceased. After cooling, the resulting precipitate is collected by filtration and washed with water. After drying and recrystallization twice from aqueous ethanol, 4-benzoyl-3-hydroxy-5-nitrobenzoic acid is obtained as a monohydrate with a melting point of 264° -266° C.

Workup

  1. stirringAfter additional stirring at -5° C to 0° C for about 15 minutes
  2. temperaturethe resulting diazoniumsolution is heated on a steam bath for 2-3 hours until the nitrogen evolution
  3. temperatureAfter cooling
  4. filtrationthe resulting precipitate is collected by filtration
  5. washwashed with water
  6. customAfter drying
  7. customrecrystallization twice from aqueous ethanol

Sources & evidence

ORD record
ord-7b15e7abd56445c29ff128b783c94e27
Source dataset
uspto-grants-1977_04
Patent number
US04018794

Reaction notes

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