Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 400360Generated: October 30, 2026

Water → Methyl 4-amino-2-(3-chloropropoxy)benzoate

https://huagongshe.com/reaction/400360

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant1-Bromo-3-chloropropaneHCID 8006—
ReactantCesium carbonateHCID 10796—
ReactantMethyl p-aminosalicylateHCID 77787—
SolventDimethylformamideHCID 6228—
ProductMethyl 4-amino-2-(3-chloropropoxy)benzoateHCID 6728489994.2%

Reaction Conditions

Temperature60 °C

Reaction Steps

To a solution of methyl 4-amino-2-hydroxybenzoate (500 mg, 2.99 mmol) and 1-bromo-3-chloropropane (0.294 mL, 2.99 mmol) in DMF (3 mL) was added CESIUM CARBONATE (1462 mg, 4.49 mmol). The resulting mixture was stirred at 60° C. for 6 hrs. The reaction mixture was poured into water, extracted with ethyl acetate, washed with brine, dried over MgSO4, concentrated. The crude product was purified by silica gel chromatography using a gradient of 20-50% EtOAc/Hexanes to give 686 mg (94%) methyl 4-amino-2-(3-chloropropoxy)benzoate.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08741884B2
Source datasetuspto-grants-2014_06
ORD IDord-3e9365e0cb77445f848d6bb4faae9222
Source noteuspto-grants-2014_06