Hydrochloric Acid → 2-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoic acid

HRID 1464174Notes

Reaction equation

HRID 1464174 reaction equation
C([O:4][C:5]1[CH:17]=[CH:16][C:15]([CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[CH:14][C:6]=1[C:7]([O:9]CC(C)C)=[O:8])(=O)C.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH2:36].S(=O)(=O)(O)O.[OH-].[K+].Cl>ClCCl.C(O)C>[OH:4][C:5]1[CH:17]=[CH:16][C:15]([CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH:36][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=3)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[CH:14][C:6]=1[C:7]([OH:9])=[O:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 104392-AminopyridineHCID 14797Potassium HydroxideHCID 53789228Isobutyl 2-acetyloxy-5-[2-(4-(chlorosulfonyl)phenyl)ethenyl]benzoate

Product 1

HCID 543430162-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Isobutyl 2-acetyloxy-5-[2-(4-(chlorosulfonyl)phenyl)ethenyl]benzoate (1.99 g, 0.0046 mol) and 2-pyridinamine (1.3 g, 0.0138 mol) was stirred in dichloromethane (10 ml) at 45° C. for 1 h. After cooling to room temperature dichloromethane (20 ml) and 2M sulfuric acid (20 ml) were added. The precipitated solid (1.3 g) was collected and washed with water. The organic phase was taken to dryness and the residue treated with boiling methanol containing ammonia (2 ml) for 20 min. After cooling, 0.6 g was collected which was combined with the first crop. The combined material (1.9 g) was refluxed with potassium hydroxide (1 g) in water (50 ml). After acidification and filtration, the solid residue was dissolved in 70% ethanol with about 3 equivalents of potassium hydroxide at the boiling point and acidified while boiling with hydrochloric acid. After filtration and drying, the yield was 1.25 g (70%).

Workup

  1. additionwere added
  2. customThe precipitated solid (1.3 g) was collected
  3. washwashed with water
  4. additionthe residue treated with boiling methanol
  5. additioncontaining ammonia (2 ml) for 20 min
  6. temperatureAfter cooling
  7. custom0.6 g was collected which
  8. temperatureThe combined material (1.9 g) was refluxed with potassium hydroxide (1 g) in water (50 ml)
  9. filtrationAfter acidification and filtration
  10. filtrationAfter filtration
  11. customdrying

Sources & evidence

ORD record
ord-234b4b41977243faaa958ff2b5483e50
Source dataset
uspto-grants-1994_04
Patent number
US05302718

Reaction notes

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