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

HRID 225716Notes

Reaction equation

HRID 225716 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 (example B1a)), step1), 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 1 N 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-9b5b83baf20949e5b4faf859fb9c208e
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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