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Ammonium Hydroxide → 2-Amino-5-methanesulfonylbenzoic acid

HRID 1820708
Notes
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Reaction equation

HRID 1820708 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 23291322-Chloro-5-(methylsulphonyl)benzoic acid2×

Product 1

HCID 230690042-Amino-5-methanesulfonylbenzoic 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 (compound 1.2a), 0.39 mmol Copper powder and 10 ml ammonium hydroxide 25% was heated at 125-130° C. with stirring for 18 hours. The 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 (, 100%)

Workup

  1. temperatureThe mixture 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-94a5b2b5287c4155800d722c6b871cec
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07605163B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes