Methanol → 3,5-Diamino-2-methylbenzoic acid

HRID 1458677Notes

Reaction equation

HRID 1458677 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH2:11])[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:16]O>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH2:11])[C:5]([O:7][CH3:16])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride2×HCID 692633,4-Diaminobenzoic acid

Product 1

HCID 1355243,5-Diamino-2-methylbenzoic acidYield 93%

Procedure

3,4-Diaminobenzoic acid (3.0 g) was suspended in methanol, followed by the dropwise addition of 1.86 ml of thionyl chloride. Thionyl chloride was added twice, in an amount of 0.5 ml each time, and the resulting mixture was heated under reflux for 10 hours and 40 minutes. The thionyl chloride and methanol were distilled out, followed by the dissolution of the residue in methylene chloride. The solution so formed was washed with a 0.5N aqueous solution of sodium hydroxide and then with a saturated aqueous solution of sodium chloride, and was dried over sodium sulfate. The solvent was distilled out. The residue was washed with n-hexane and then dried, whereby 3.04 g of the target compound were obtained (yield: 93%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 10 hours and 40 minutes
  3. distillationThe thionyl chloride and methanol were distilled out
  4. dissolutionfollowed by the dissolution of the residue in methylene chloride
  5. customThe solution so formed
  6. washwas washed with a 0.5N aqueous solution of sodium hydroxide
  7. dry with materialwith a saturated aqueous solution of sodium chloride, and was dried over sodium sulfate
  8. distillationThe solvent was distilled out
  9. washThe residue was washed with n-hexane
  10. customdried

Sources & evidence

ORD record
ord-97091eb39e8a44b38b4221debb9be6ef
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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