Hydrochloric Acid → 7-(2,3-Dihydroxypropyl)-6-methoxy-1,2,3,4-tetrahydroquinolin-2-one

HRID 494985Notes

Reaction equation

HRID 494985 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]3)=[CH:10][C:9]=2[O:19][CH3:20])[CH2:4][O:3]1.Cl>CO.O1CCCC1>[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]2)=[CH:10][C:9]=1[O:19][CH3:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 576827707-((2,2-Dimethyl-[1,3]dioxolan-4-yl)methyl)-6-methoxy-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 576827997-(2,3-Dihydroxypropyl)-6-methoxy-1,2,3,4-tetrahydroquinolin-2-oneYield 117%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

109 mg of 7-((2,2-dimethyl-[1,3]dioxolan-4-yl)methyl)-6-methoxy-1,2,3,4-tetrahydroquinolin-2-one was dissolved in 4 ml of methanol-tetrahydrofuran (1:1). While cooling on ice, 1 ml of 2 N hydrochloric acid was added to the reaction solution, and the obtained mixture was then stirred at room temperature for 3 hours. Thereafter, the reaction solution was concentrated under a reduced pressure, so as to obtain 110 mg of 7-(2,3-dihydroxypropyl)-6-methoxy-1,2,3,4-tetrahydroquinolin-2-one. This compound was directly used in the following reaction without further purification.

Workup

  1. additionwas added to the reaction solution
  2. concentrationThereafter, the reaction solution was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-6bd0b2331ed241c49c0867b09d98d27b
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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