Sulfamic Acid → 5-Methoxy-2-nitrobenzoic acid

HRID 2255883Notes

Reaction equation

HRID 2255883 reaction equation
S(=O)(=O)(O)N.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([N+:16]([O-:18])=[O:17])=[C:12]([CH:15]=1)[CH:13]=[O:14].CC(C)=[O:21].O.Cl([O-])=O.[Na+]>O>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([N+:16]([O-:18])=[O:17])=[C:12]([CH:15]=1)[C:13]([OH:21])=[O:14]

Participants

6

Reactant 4

HCID 5987Sulfamic AcidHCID 2303715-Methoxy-2-nitrobenzaldehydeHCID 18366337Propan-2-one--water (1/1)HCID 23668197Sodium Chlorite

Product 1

HCID 3392095-Methoxy-2-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sulfamic acid (15.73 g, 0.162 mol) is added to a solution of 5-methoxy-2-nitrobezaldehyde (19.6 g, 0.108 mol) in an acetone/water (1:1) mixture. Sodium chlorite (18.31 g, 80% real, 0.162 mol) is then added to the reaction mixture at a rate which maintains the reaction mixture temperature below 40° C. The resultant reaction mixture is stirred at room temperature for 24 hours and poured into water. The aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with 2N hydrochloric acid and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title product as a yellow solid.

Workup

  1. customthe reaction mixture temperature below 40° C
  2. customThe resultant reaction mixture
  3. extractionThe aqueous mixture is extracted with ethyl acetate
  4. washwashed sequentially with 2N hydrochloric acid and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d0c4044aa35f48bc84e5c1c5aa3ec281
Source dataset
uspto-grants-1997_08
Patent number
US05654256

Reaction notes

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