Methanol → Methyl 5-nitrosalicylate

HRID 2228292Notes

Reaction equation

HRID 2228292 reaction equation
[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(=O)(=O)(O)O.[CH3:19]O>>[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([O:11][CH3:19])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 73185-Nitrosalicylic acid

Product 1

HCID 87041Methyl 5-nitrosalicylateYield 72%

Conditions

Temperature
100 °C

Procedure

In methanol (250 ml) was suspended 5-nitrosalicylic acid (50.0 g, 273 mmol), and to the mixture was added sulfuric acid (6 ml). The mixture was stirred at 100° C. for 24 hours and the cooled to room temperature. The precipitated insoluble materials were filtered, which were washed with hydrous methanol (containing 20% of water) and methanol, and dried under reduced pressure to give methyl 5-nitrosalicylate (38.5 g, 195 mmol, 72%).

Workup

  1. temperaturethe cooled to room temperature
  2. filtrationThe precipitated insoluble materials were filtered
  3. washwhich were washed with hydrous methanol (containing 20% of water) and methanol
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-e82a74493e9245488920fa5579300639
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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