Triethylamine → Methyl 3-amino-5-(methylsulfonyl)benzoate

HRID 399790Notes

Reaction equation

HRID 399790 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:15]([CH3:18])(=[O:17])=[O:16].C(N(CC)CC)C>CO.O1CCCC1.[C].[Pd]>[NH2:12][C:11]1[CH:2]=[C:3]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:4]=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 18945451Methyl 4-chloro-3-methylsulfonyl-5-nitrobenzoate

Product 1

HCID 18945412Methyl 3-amino-5-(methylsulfonyl)benzoateYield 78.9%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium-carbon (2.5 g) was added to a mixture of methyl 4-chloro-3-methylsulfonyl-5-nitrobenzoate (9.5 g) and triethylamine (5.0 ml) in methanol (150 ml) and tetrahydrofuran (100 ml), and the mixture was subjected to catalytic reduction at ambient temperature under atmospheric pressure. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. To the residue was added a mixture of ethyl acetate and water, and adjusted to pH 9 with 20% aqueous potassium carbonate solution. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give methyl 5-amino-3-methylsulfonylbenzoate (5.85 g).

Workup

  1. customwas subjected to catalytic reduction at ambient temperature under atmospheric pressure
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. additionTo the residue was added
  5. additiona mixture of ethyl acetate and water
  6. washThe separated organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-1aedb774c2ef40a6a5d8b43c0699b05c
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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