Methanol → 499157-23-2

HRID 1726317Notes

Reaction equation

HRID 1726317 reaction equation
S(Cl)([Cl:3])=O.[OH:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[NH2:15])[C:9]([OH:11])=[O:10].[CH3:16]O>>[ClH:3].[CH3:16][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([NH2:15])=[C:6]([OH:5])[CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1375664-Amino-3-hydroxybenzoic acid

Product 1

HCID 56587758499157-23-2

Procedure

To an anhydrous methanol (100 ml) was added thionyl chloride (14.0 ml) at −10° C. during 20 minutes. After stirring the mixture for 15 minutes, 3-hydroxy-4-aminobenzoic acid (10.0 g) was added at the same temperature. The appeared suspension was stirred at room temperature overnight. The mixture was concentrated and then azeotroped with methanol (50 ml, twice). To the residue was added diethyl ether, and the residue was collected by suction filtration in washing with diethyl ether to give the title compound (12.8 g) having the following physical data.

Workup

  1. stirringThe appeared suspension was stirred at room temperature overnight
  2. concentrationThe mixture was concentrated
  3. customazeotroped with methanol (50 ml
  4. additionTo the residue was added diethyl ether
  5. filtrationthe residue was collected by suction filtration
  6. washin washing with diethyl ether

Sources & evidence

ORD record
ord-4383bfec10314571ab6e29fea0350621
Source dataset
uspto-grants-2009_02
Patent number
US07491748B2

Reaction notes

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