Methanol → Methyl p-aminosalicylate

HRID 1650371Notes

Reaction equation

HRID 1650371 reaction equation
[Na+].[NH2:2][C:3]1[CH:4]=[C:5]([OH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([O-:9])=[O:8].[CH3:13]O>Cl>[NH2:2][C:3]1[CH:4]=[C:5]([OH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([O:9][CH3:13])=[O:8]

Participants

4

Reactant 2

HCID 887MethanolHCID 2724368Aminosalicylate sodium anhydrous

Product 1

HCID 77787Methyl p-aminosalicylate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a solution of 25 g (118.5 mmol) of 4-aminosalicylic acid sodium salt in 250 ml of methanol is bubbled in anhydrous HCl gas at room temperature. Addition of HCl gas is continued for 30 minutes. Excess methanol is removed in vacuo and the residue taken up in ethyl acetate and washed with saturated aqueous NaHCO3. The organic layer is dried over MgSO4, filtered and concentrated, giving methyl 4-aminosalicylate which is used directly in the next step.

Workup

  1. customExcess methanol is removed in vacuo
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c048b0315b624c1d92bb194c2233abc3
Source dataset
uspto-grants-1990_05
Patent number
US04924010

Reaction notes

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