Methanol → Methyl 3,5-diaminobenzoate

HRID 1458693Notes

Reaction equation

HRID 1458693 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([NH2:15])[CH:14]=1)[C:9]([OH:11])=[O:10].[CH3:16]O>>[NH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([NH2:15])[CH:14]=1)[C:9]([O:11][CH3:16])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 120623,5-Diaminobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 7010431Methyl 3,5-diaminobenzoateYield 60%

Procedure

Thionyl chloride (3.7 g) was added dropwise under ice cooling to a solution of 5.0 g (33 mmol) of 3,5-diaminobenzoic acid in 250 ml of methanol, followed by stirring at room temperature for 2 hours and then stirring under heating and reflux for additional 6 hours. After the solvent was distilled out under reduced pressure, the residue was neutralized with aqueous ammonia and then extracted with methylene chloride. The extract was dried over sodium sulfate and then dried up under reduced pressure, whereby 3.3 g of white powder were obtained (yield: 60%).

Workup

  1. stirringstirring
  2. temperatureunder heating
  3. temperaturereflux for additional 6 hours
  4. distillationAfter the solvent was distilled out under reduced pressure
  5. extractionextracted with methylene chloride
  6. dry with materialThe extract was dried over sodium sulfate
  7. customdried up under reduced pressure

Sources & evidence

ORD record
ord-52c2d1256e88490d963fed9e3a138d75
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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