3-(6-Methyl-5-nitro-2-pyridinyl)-1,3-oxazolidin-2-one → 3-(5-Amino-6-methyl-2-pyridinyl)-1,3-oxazolidin-2-one

HRID 594097

Reaction equation

HRID 594097 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][O:10][C:9]2=[O:13])[CH:5]=[CH:4][C:3]=1[N+:14]([O-])=O>[Pd]>[NH2:14][C:3]1[CH:4]=[CH:5][C:6]([N:8]2[CH2:12][CH2:11][O:10][C:9]2=[O:13])=[N:7][C:2]=1[CH3:1]

Participants

3

Reactant 1

HCID 898762173-(6-Methyl-5-nitro-2-pyridinyl)-1,3-oxazolidin-2-one2×

Product 1

HCID 898760323-(5-Amino-6-methyl-2-pyridinyl)-1,3-oxazolidin-2-oneYield 89.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 3-(6-methyl-5-nitro-2-pyridinyl)-1,3-oxazolidin-2-one (which may be prepared, for example, according to Intermediate 3) (200 mg, 0.896 mmol) was stirred rapidly over 10% palladium on carbon (30 mg, 0.028 mmol) under an atmosphere of hydrogen at room temperature for 3 hours. The catalyst was then removed by filtration through a pad of celite. The filtrate was evaporated in vacuo to give the title compound (155 mg) as a white solid. LCMS (2 min, formic) Rt 0.38 min, m/z (ES+) 194 (M+H).

Workup

  1. customThe catalyst was then removed by filtration through a pad of celite
  2. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-2ce60ad43aa746439a4c6972f9644118
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Linked notes

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