Pyridine → HCID 12408786, compound

HRID 328934Notes

Reaction equation

HRID 328934 reaction equation
[C:1]([C:9]1[C:17]([N+:18]([O-])=O)=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[O:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[NH2:18][C:17]1[C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:11]=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24489Sodium DithioniteHCID 21440130HCID 21440130, compound

Product 1

HCID 12408786HCID 12408786, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 4-benzoyl-3-n-butoxy-5-nitrobenzoic acid (5.1 g), pyridine (25 ml), and water (25 ml), sodium dithionite (10.2 g) is added in portions. The mixture is heated on a steam bath for 1 hour and is then evaporated in vacuo. The remaining material is dissolved in water (about 50 ml) and the solution is acidified with conc. hydrochloric acid (about 15 ml). After cooling, the resulting precipitate is collected by filtration and washed with water. After drying and recrystallization twice from ethanol, 5-amino-4-benzoyl-3-n-butoxybenzoic acid is obtained with a melting point of 202.5° -203.5° C.

Workup

  1. additionis added in portions
  2. temperatureThe mixture is heated on a steam bath for 1 hour
  3. customis then evaporated in vacuo
  4. dissolutionThe remaining material is dissolved in water (about 50 ml)
  5. temperatureAfter cooling
  6. filtrationthe resulting precipitate is collected by filtration
  7. washwashed with water
  8. customAfter drying
  9. customrecrystallization twice from ethanol

Sources & evidence

ORD record
ord-cbab8259fe0b45509e2495d6ad94b225
Source dataset
uspto-grants-1977_04
Patent number
US04018794

Reaction notes

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