Sodium Dithionite → 5-Amino-3-benzylamino-4-phenylbenzoic acid

HRID 1605544Notes

Reaction equation

HRID 1605544 reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([N+:24]([O-])=O)[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>N1C=CC=CC=1.O>[NH2:24][C:16]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 124087723-Benzylamino-5-nitro-4-phenylbenzoic acid

Product 1

HCID 124087755-Amino-3-benzylamino-4-phenylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a stirred solution of 3-benzylamino-5-nitro-4-phenylbenzoic acid (3.0 g) in a mixture of pyridine (15 ml) and water (15 ml), sodium dithionite (6.0 g) is added in portions during about 15 minutes. The mixture is heated on a steam bath for about 30 minutes, and is then evaporated in vacuo. The residue is treated with cold 1 N acetic acid (about 50 ml) and after cooling, the resulting precipitate is collected by filtration, washed with water and dried. After recrystallization twice from aqueous ethanol, 5-amino-3-benzylamino-4-phenylbenzoic acid is obtained with a melting point of 179°-181° C.

Workup

  1. additionis added in portions during about 15 minutes
  2. temperatureThe mixture is heated on a steam bath for about 30 minutes
  3. customis then evaporated in vacuo
  4. additionThe residue is treated with cold 1 N acetic acid (about 50 ml)
  5. temperatureafter cooling
  6. filtrationthe resulting precipitate is collected by filtration
  7. washwashed with water
  8. customdried
  9. customAfter recrystallization twice from aqueous ethanol

Sources & evidence

ORD record
ord-9ccb8f0ee595416895333397c0f562a4
Source dataset
uspto-grants-1976_04
Patent number
US03950380

Reaction notes

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