Sulfamic Acid → 5-Methoxy-4-nitropicolinic Acid

HRID 2370871Notes

Reaction equation

HRID 2370871 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:11]([O-:13])=[O:12])=[CH:5][C:6]([CH:9]=[O:10])=[N:7][CH:8]=1.Cl([O-])=[O:15].[Na+].S(=O)(=O)(O)N.CCOC(C)=O>CC(C)=O.O>[CH3:1][O:2][C:3]1[C:4]([N+:11]([O-:13])=[O:12])=[CH:5][C:6]([C:9]([OH:15])=[O:10])=[N:7][CH:8]=1

Participants

7

Reactant 4

HCID 5987Sulfamic AcidHCID 8857Ethyl AcetateHCID 23668197Sodium ChloriteHCID 866879995-Methoxy-4-nitropicolinaldehyde

Product 1

HCID 866880005-Methoxy-4-nitropicolinic Acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 5-methoxy-4-nitropicolinaldehyde (4 g, 0.02 mol) in acetone and water (1:1, 100 mL) was added sodium chlorite (5.9 g, 0.065 mol, spectrochem, india) and sulfamic acid (6.3 g, 0.065 mol, Rankem, India) and the reaction mixture was stirred for 1 h at rt. Reaction progress was monitored by TLC (50% EtOAc in petroleum ether). After completion, the reaction mixture was concentrated to get a white precipitate which was filtered and dried to afford the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.6 (brs, 1H) 8.90 (s, 1H), 8.41 (s, 1H), 4.15 (s, 3H). MS (ESI, positive ion) m/z: 197.8 (M+H).

Workup

  1. customReaction progress
  2. concentrationAfter completion, the reaction mixture was concentrated
  3. customto get a white precipitate which
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-afee4334fa874f158819e2c94af60513
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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