Methanol → Methyl 5-nitrosalicylate

HRID 1583251Notes

Reaction equation

HRID 1583251 reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[CH:16]=[C:12]([C:13]([OH:15])=[O:14])[C:11]([OH:17])=[CH:10][CH:9]=1)([O-:7])=[O:6].[CH3:18]O>>[CH3:18][O:14][C:13](=[O:15])[C:12]1[CH:16]=[C:8]([N+:5]([O-:7])=[O:6])[CH:9]=[CH:10][C:11]=1[OH:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 73185-Nitrosalicylic acidHCID 24386Thionyl Chloride2×

Product 1

HCID 87041Methyl 5-nitrosalicylate

Procedure

Thionyl chloride (30 ml) was added dropwise to a solution of 5-nitro salicyclic acid (25 g) in methanol (300 ml) over 30 minutes. After stirring at room temperature for 18 hours the solvent and excess thionyl chloride was removed on a rotary evaporator. The residue was dissolved in hot toluene, filtered and cooled. A white solid methyl-2-hydroxy-5-nitro-benzoate was isolated by filtration. This material was treated with acetic anhydride (20 ml) and sulfuric acid (8 drops) at 50° C. for 1 hour. The reaction was cooled, poured into cold water (250 ml), stirred for 30 minutes and the title compound was isolated by vacuum filtration. This material was washed well with water, m.p. ca. 70°-72° C.

Workup

  1. customwas removed on a rotary evaporator
  2. dissolutionThe residue was dissolved in hot toluene
  3. filtrationfiltered
  4. temperaturecooled

Sources & evidence

ORD record
ord-a308f451fa18435a8c9b4ac8e9c1c10b
Source dataset
uspto-grants-1985_11
Patent number
US04551279

Reaction notes

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