Hydrogen chloride-ethyl acetate → HCID 22736935, compound

HRID 50862Notes

Reaction equation

HRID 50862 reaction equation
[F:1][C:2]1[C:11]([CH:12]([OH:29])[CH2:13][N:14]2[CH2:19][CH2:18][C:17]([OH:28])([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:30])[NH:7]2.[ClH:31].CCOC(C)=O>CO>[ClH:31].[F:1][C:2]1[C:11]([CH:12]([OH:29])[CH2:13][N:14]2[CH2:15][CH2:16][C:17]([OH:28])([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=3)[CH2:18][CH2:19]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:30])[NH:7]2

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 22736936HCID 22736936, compound

Product 1

HCID 22736935HCID 22736935, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5-Fluoro-6-[1-hydroxy-2-[4-hydroxy-4-(3-methoxyphenyl)-1-piperidinyl]ethyl]-3,4-dihydroquinolin-2(1H)-one (216 mg, 0.522 mmol) in methanol (5 ml) was added 4N HCl-AcOEt (137 μl, 0.548 mmol) and the mixture was concentrated in vacuo. The residue was crystallized twice from 2-propanol to afford 5-Fluoro-6-[1-hydroxy-2-[4-hydroxy-4-(3-methoxyphenyl)-1-piperidinyl]ethyl]-3,4-dihydroquinolin-2(1H)-one hydrochloride as a white solid (190 mg, 81%).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was crystallized twice from 2-propanol

Sources & evidence

ORD record
ord-32b73139adac435d90bbc701511cc9eb
Source dataset
uspto-grants-2004_03
Patent number
US06713490B2

Reaction notes

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