Hydrochloric Acid → Ethyl 4-amino-3-methoxybenzoate

HRID 377139Notes

Reaction equation

HRID 377139 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].Cl.[CH3:14][CH2:15]O>>[CH2:14]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([NH2:1])=[C:3]([O:11][CH3:12])[CH:4]=1)[CH3:15]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 2880572486-69-3

Product 1

HCID 11788808Ethyl 4-amino-3-methoxybenzoate

Procedure

To a solution of 3.343 g (20 mmole) of 4-amino-3-methoxybenzoic acid in 200 mL EtOH is bubbled a stream of HCl gas for three minutes. The HCl saturated solution is stirred at room temperature for two days. Solvent is evaporated under vacuum and the resulting residue is dissolved in 100 mL water. The water layer is basified with K2CO3 and extracted with CH2Cl2 (3×200 mL). The combined CH2Cl2 layer is washed with saturated NaHCO3 (200 mL), brine and then dried over MgSO4, filtered and evaporated under reduced pressure to give the desired product.

Workup

  1. customSolvent is evaporated under vacuum
  2. dissolutionthe resulting residue is dissolved in 100 mL water
  3. extractionextracted with CH2Cl2 (3×200 mL)
  4. washThe combined CH2Cl2 layer is washed with saturated NaHCO3 (200 mL), brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-eeb55cbf41694783a377dc16cb25b25a
Source dataset
uspto-grants-2000_02
Patent number
US06024937

Reaction notes

Loading…