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Methanol → Methyl 3-amino-5-[methyl(methylsulfonyl)amino]benzoate

HRID 1160449
Notes
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Reaction equation

HRID 1160449 reaction equation
[CH3:1][N:2]([S:16]([CH3:19])(=[O:18])=[O:17])[C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:13]([O-])=O)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].CO>[Pd].C(OCC)(=O)C>[NH2:13][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([N:2]([CH3:1])[S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 887MethanolHCID 57815130Methyl 3-[(methanesulfonyl)(methyl)amino]-5-nitrobenzoate

Product 1

HCID 21054739Methyl 3-amino-5-[methyl(methylsulfonyl)amino]benzoateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 3-[methyl(methylsulfonyl)amino]-5-nitrobenzoate obtained in Reference Example 95.76 g (20 mmol), 10% Pd/C (50% wet) (1.50 g), methanol (80 mL) and ethyl acetate (80 mL) was stirred at room temperature under hydrogen atmosphere for 1.5 hours. The reaction solution was filtered on Celite and the solvent was evaporated to give 5.11 g (19.8 mmol) of the title compound (yield: 99%).

Workup

  1. filtrationThe reaction solution was filtered on Celite
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6d79eb5f11344096a452566a6dec06c5
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07816387B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes