Ethanol → Ethyl 4-amino-5-chloro-2-methoxybenzoate

HRID 630383Notes

Reaction equation

HRID 630383 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[CH2:14](O)[CH3:15].[OH-].[Na+]>Cl>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([O:8][CH2:14][CH3:15])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 816264-Amino-5-chloro-2-methoxybenzoic acid

Product 1

HCID 732631Ethyl 4-amino-5-chloro-2-methoxybenzoateYield 78%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-amino-5-chloro-2-methoxybenzoic acid (6.6 g, 0.031 mol) in hydrogen chloride 1.25M in Ethanol (250 mL, 0.31 mol) was stirred in a pressure vessel for 6 h at 65° C. The reaction mixture was basified with sodium hydroxide 2N and extracted with methylene chloride. The organic layer was washed with water, dried and filtered. The solvent was removed under reduced pressure giving the title compound as a white solid (78%), which was used in the next step without further purification.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with water
  3. customdried
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-982c94fe1a004a5f81aa26c54262d321
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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