Methanol → Methyl 5-sulfamoylpyridine-2-carboxylate

HRID 331186Notes

Reaction equation

HRID 331186 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1)#N.[C:13](=O)(O)[O-:14].[Na+].C[OH:19]>Cl.O>[NH2:12][S:9]([C:6]1[CH:5]=[CH:4][C:3]([C:1]([O:14][CH3:13])=[O:19])=[N:8][CH:7]=1)(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 576254346-Cyanopyridine-3-sulfonamide

Product 1

HCID 57625382Methyl 5-sulfamoylpyridine-2-carboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

6-Cyanopyridine-3-sulfonamide (10 g, 0.0545 mol) is dissolved in dry HCl in methanol (400 ml) at 25-26° C. under nitrogen atmosphere. Reaction mixture is heated to 50° C. and stirred for 15 h at 50° C. The reaction mixture is concentrated under vacuum and the residue obtained is diluted with water (100 ml) and basified with solid sodium bicarbonate to pH 6-7. The reaction mixture is stirred for 15 minutes and filtered. The resulting solid obtained is washed with water (50 ml) and dried under vacuum to afford the title compound (9 g, 76%) as light yellow solid. 1H NMR (DMSO-d6) δ 9.08 (d, J=3 Hz, 1H), 8.38 (dd, J=9 and 3 Hz, 1H), 8.26 (d, J=9 Hz, 1H), 7.79 (m, 2H), 3.93 (s, 3H). HPLC (max plot) 94%; Rt 3.45 min; LC/MS: (ES+) 216.9.

Workup

  1. customReaction mixture
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. customthe residue obtained
  4. stirringThe reaction mixture is stirred for 15 minutes
  5. filtrationfiltered
  6. customThe resulting solid obtained
  7. washis washed with water (50 ml)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-ff9a14e9fbbd4d96af986c1eaedc30d8
Source dataset
uspto-grants-2014_11
Patent number
US08877757B2

Reaction notes

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