Hydrochloric Acid → 3-Amino-5-nitro-4-phenylbenzoic acid

HRID 1605542Notes

Reaction equation

HRID 1605542 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:19]([O-])=O)[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl>N1C=CC=CC=1.O>[NH2:19][C:11]1[CH:10]=[C:6]([CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 124087663,5-Dinitro-4-phenylbenzoic acid

Product 1

HCID 124087693-Amino-5-nitro-4-phenylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a stirred solution of 3,5-dinitro-4-phenylbenzoic acid (135 g) in a mixture of pyridine (625 ml) and water (625 ml), sodium dithionite (235 g) is added in portions during about 30 minutes, keeping the temperature at 12°-15° C by external cooling. After additional stirring at this temperature for about 15 minutes, the resulting solution is acidified by the addition of conc. hydrochloric acid (750 ml), keeping the temperature below 25° C by the addition of ice to the reaction mixture. The mixture is left for about 20 hours, and the resulting precipitate is then collected by filtration, washed with water and dried. After recrystallization from aqueous ethanol, 3-amino-5-nitro-4-phenylbenzoic acid is obtained with a melting point of 247°-249° C (dec.).

Workup

  1. additionis added in portions during about 30 minutes
  2. customat 12°-15° C
  3. customthe temperature below 25° C
  4. additionby the addition of ice to the reaction mixture
  5. waitThe mixture is left for about 20 hours
  6. filtrationthe resulting precipitate is then collected by filtration
  7. washwashed with water
  8. customdried
  9. customAfter recrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-954b84b002164923a87f2fa225187a1e
Source dataset
uspto-grants-1976_04
Patent number
US03950380

Reaction notes

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