Ammonium Hydroxide → 2-Amino-5-(methanesulfonyl)benzoic acid

HRID 2251161Notes

Reaction equation

HRID 2251161 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[NH4+:16]>[Cu]>[NH2:16][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 23291322-Chloro-5-(methylsulphonyl)benzoic acid

Product 1

HCID 230690042-Amino-5-(methanesulfonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
127.5 °C

Procedure

A mixture of 4.26 mmol 2-chloro-5-methanesulfonyl-benzoic acid, 0.39 mmol Copper powder and 10 ml ammonium hydroxide 25% was heated at 125-130° C. with stirring for 18 hours. Mixture was cooled to room temperature and filtered. The solid was washed with methanol. The filtrate was concentrated in vacuo. The residue was acidified with HCl 1N to pH=2. The obtained solid was washed with water and dried (HV, 50° C., 1 hour) to yield the title compound MS (m/e): 214.1 (M−H, 100%)

Workup

  1. temperatureMixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe solid was washed with methanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. washThe obtained solid was washed with water
  6. customdried (HV, 50° C., 1 hour)

Sources & evidence

ORD record
ord-da2f970bd3724c6baf72098b2ff73a7d
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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