Water → HCID 58492500, compound

HRID 1474552Notes

Reaction equation

HRID 1474552 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:30])[C:5]([C:22]1[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=1)=[CH:6][N:7]2[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].ClCCl.B(Br)(Br)Br.O>ClCCl>[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:30])[C:5]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)=[CH:6][N:7]2[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 22277759Boron tribromide dichloromethaneHCID 58492440HCID 58492440, compound

Product 1

HCID 58492500HCID 58492500, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl [5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]acetate (4.0 g, 9.6 mmol) was dissolved in dichloromethane (20 ml). A 1M-boron tribromide dichloromethane solution (35 ml, 35 mmol) was added dropwise to the dissolution at −10° C. After stirring at the same temperature for 2 hours, water was added to the reaction mixture, followed by extraction with dichloromethane. The thus-obtained organic layer was concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=50:1→15:1). The purified product was concentrated to dryness under reduced pressure, giving a yellow powder of ethyl [5-fluoro-3-(4-hydroxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]acetate (2.7 g, yield: 57%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. concentrationThe thus-obtained organic layer was concentrated under reduced pressure
  3. customThe residue was purified
  4. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c3eb39cd89284621a84fffa9353edd18
Source dataset
uspto-grants-2015_04
Patent number
US09018229B2

Reaction notes

Loading…