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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1502209Generated: October 30, 2026

Hydrochloric Acid → 2-Amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoic acid

https://huagongshe.com/reaction/1502209

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantPotassium HydroxideHCID 14797—
Reactant(5E)-5-{(2E)-2-[(1-bromo-2-methylindolizin-3-yl)carbonyl]but-2-en-1-ylidene}-4-methylidene-2-phenyl-4,5-dihydro-6H-1,3-oxazin-6-oneHCID 117761369—
SolventWaterHCID 962—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Product2-Amino-5-[(1-bromo-2-methylindolizin-3-yl)carbonyl]benzoic acidHCID 66653173109.4%

Reaction Steps

The (5E)-5-{(2E)-2-[(1-bromo-2-methylindolizin-3-yl)carbonyl]but-2-en-1-ylidene}-4-methylidene-2-phenyl-4,5-dihydro-6H-1,3-oxazin-6-one (18.6 g; 40.4 mmol) is added portionwise to potassium hydroxide (22.7 g; 0.40 mol) in 100 mL of water and 140 mL of NMP. The reaction mixture is heated at reflux for 18 h, cooled to ambient temperature and poured into a hydrochloric acid solution (1 M). The yellow precipitate formed is filtered off and dried under vacuum to give 16.5 g (99%) of a yellow powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09206177B2
Source datasetuspto-grants-2015_12
ORD IDord-7ba755a81a094572a9e825f06db68e24
Source noteuspto-grants-2015_12