Sodium Carbonate → 2-((6-Methoxy-5-nitropyridin-3-yl)methylsulfonyl)acetic acid

HRID 72649

Reaction equation

HRID 72649 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][S:10]([CH2:13][C:14]([O-:16])=[O:15])(=[O:12])=[O:11])=[CH:5][C:4]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>O.CO>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][S:10]([CH2:13][C:14]([OH:16])=[O:15])(=[O:12])=[O:11])=[CH:5][C:4]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 67994885HCID 67994885, compound

Product 1

HCID 679948792-((6-Methoxy-5-nitropyridin-3-yl)methylsulfonyl)acetic acidYield 98.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-((6-methoxy-5-nitropyridin-3-yl)methylsulfonyl)acetate (1.83 g, 6 mmol) and sodium carbonate (1.8 g, 15 mmol) in a mixture of water (10 mL) and methanol (10 mL) was stirred at room temperature for 4 hours. After evaporated to dryness, the residue was acidized by dropwise addition of 1N aq. HCl. White solid was precipitated gradually as pH was brought to 2 and filtrated to give the pure product (1.72 g, 98.7%). M.p. 183-186° C.; 1H-NMR (DMSO-d6): δ 4.06 (s, 3H, OCH3), 4.13 (s, 2H, CH2), 4.79 (s, 2H, CH2), 8.48 (d, 1H J=2.0 Hz, Py-H), 8.50 (d, 1H, J=2.0 Hz, Py-H); 13C-NMR (DMSO-d6): δ 55.07, 55.41, 57.15, 118.45, 133.64, 137.96, 154.26, 156.23, 164.88; HR-MS (ESI+) m/z: 289.0064 [M+H]+; C9H10N2O7S requires 290.0209

Workup

  1. customAfter evaporated to dryness
  2. additionthe residue was acidized by dropwise addition of 1N aq. HCl
  3. customWhite solid was precipitated gradually as pH
  4. filtrationfiltrated

Sources & evidence

ORD record
ord-dcb7d44e2b8a44259ad7ba17e15535d8
Source dataset
uspto-grants-2014_09
Patent number
US08829003B2

Linked notes

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