Sodium Formate → 3-Formylamino-2-hydroxy-benzoic Acid Methyl Ester

HRID 2415791Notes

Reaction equation

HRID 2415791 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:5](=[C:7]([NH2:11])[CH:8]=[CH:9][CH:10]=1)[OH:6].[CH:13]([O-])=[O:14].[Na+]>C(O)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][CH:13]=[O:14])[C:5]=1[OH:6]

Participants

4

Reactant 2

HCID 2723810Sodium FormateHCID 12782444Methyl 3-amino-2-hydroxybenzoate

Product 1

HCID 167564653-Formylamino-2-hydroxy-benzoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a solution of methyl-3-aminosalicylate (3.34 grams, 20 mmol) in concentrated formic acid (20 mL) was added solid sodium formate (1.36 grams, 20 mmol, 1 eq.) and the resulting suspension stirred under reflux for 2 hours. The precipitate was filtered at room temperature and washed with water until neutral. After drying on air, 3.595 grams (92%) light brown crystals were collected. M+196, M−194.

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationThe precipitate was filtered at room temperature
  3. washwashed with water until neutral
  4. customAfter drying on air, 3.595 grams (92%) light brown crystals
  5. customwere collected

Sources & evidence

ORD record
ord-c7c2770ad81e4f478c09aa901e004454
Source dataset
uspto-grants-2004_11
Patent number
US06821977B2

Reaction notes

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