Methanol → Methyl 4-amino-3,5-dichlorobenzoate

HRID 1502790Notes

Reaction equation

HRID 1502790 reaction equation
OS(O)(=O)=O.[NH2:6][C:7]1[C:15]([Cl:16])=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[Cl:17].[CH3:18]O>>[NH2:6][C:7]1[C:8]([Cl:17])=[CH:9][C:10]([C:11]([O:13][CH3:18])=[O:12])=[CH:14][C:15]=1[Cl:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 420614-Amino-3,5-dichlorobenzoic acid

Product 1

HCID 604808Methyl 4-amino-3,5-dichlorobenzoateYield 70%

Conditions

Temperature
80 °C

Procedure

conc. H2SO4 (2.5 mL, 97.04 mmol) was added drop wise to a stirred solution of 4-amino-3,5-dichlorobenzoic acid (10.0 g, 48.54 mmol) in MeOH (150 mL) at 0° C. and the reaction mixture was then stirred at 80° C. for 8 h. The volatiles were evaporated; ice-water was added to the residue and extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to afford the title compound as a white solid (7.5 g, 70%): 1H NMR (300 MHz, DMSO-d6) δ 8.05 (s, 2H), 3.96 (s, 3H); ESIMS m/z 282 ([M]+); IR (KBr): 1733, 762, 514 cm−1.

Workup

  1. customThe volatiles were evaporated
  2. additionice-water was added to the residue
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-342532572b8d4abf9da7bf3db4ae01b7
Source dataset
uspto-grants-2015_12
Patent number
US09210927B2

Reaction notes

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