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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1376147Generated: October 31, 2026

Hydrochloric Acid → 5-Chloro-N-{1-[3-hydroxy-2-(hydroxymethyl)propyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide

https://huagongshe.com/reaction/1376147

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
Reactant5-Chloro-N-{1-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamideHCID 10238683—
SolventTetrahydrofuranHCID 8028—
Product5-Chloro-N-{1-[3-hydroxy-2-(hydroxymethyl)propyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamideHCID 1031013885%

Reaction Steps

6M aqueous HCl (2.34 mL) was added to 5-chloro-N-{1-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide (Example 37; 540 mg, 1.16 mmol) in THF (19 mL) and the reaction was stirred for 1 h. The reaction was quenched by addition of triethylamine (1.5 mL) and the reaction was diluted with water (20 mL) and EtOAc (40 mL). The organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was triturated with hot Et2O (15 mL) and after cooling was filtered and dried to afford the title compound (421 mg, 85%) as white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07169927B2
Source datasetuspto-grants-2007_01
ORD IDord-04f9d429acdd44628b0d0391643c3ac0
Source noteuspto-grants-2007_01