Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2208744Generated: November 1, 2026

Ammonium Chloride → Methyl 3-Amino-5-bromo-2-methylbenzoate

https://huagongshe.com/reaction/2208744

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmonium ChlorideHCID 25517—
ReactantMethyl 5-bromo-2-methyl-3-nitrobenzoateHCID 24727998—
CatalystIronHCID 23925—
SolventEthanolHCID 702—
SolventSodium BicarbonateHCID 516892—
ProductMethyl 3-Amino-5-bromo-2-methylbenzoateHCID 2472918199.1%

Reaction Conditions

Temperature90 °C

Reaction Steps

To a stirred solution of methyl 5-bromo-2-methyl-3-nitrobenzoate (17 g, 62.04 mmol) in ethanol (85 mL), was added NH4Cl solution (17 g in 85 mL water, 317.8 mmol) followed by Fe powder (27.82 g, 498.11 mmol). Resulting reaction mass was stirred at 90° C. for 1 h. On completion, reaction mass was filtered and filtrate was concentrated till dryness to get solid which was dissolved in saturated sodium bicarbonate solution. Aqueous layer was extracted with ethyl acetate. Combined organic layers were dried over sodium sulfate and concentrated to afford the desired compound (15 g, 99%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09376422B2
Source datasetuspto-grants-2016_06
ORD IDord-6a5aa48243e84381ab5a1207cdf40c4a
Source noteuspto-grants-2016_06