Water → HCID 58492500, compound

HRID 68163Notes

Reaction equation

HRID 68163 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][N:6]1[C:15]2[C:10](=[C:11]([F:20])[CH:12]=[CH:13][C:14]=2[O:16][CH2:17][CH2:18][CH3:19])[C:9](=[O:21])[C:8]([C:22]2[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=2)=[CH:7]1)[CH3:2].ClCCl.B(Br)(Br)Br.O>ClCCl>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][N:6]1[C:15]2[C:10](=[C:11]([F:20])[CH:12]=[CH:13][C:14]=2[O:16][CH2:17][CH2:18][CH3:19])[C:9](=[O:21])[C:8]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[CH:7]1)[CH3:2]

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-c1973c650c5a4c0ba36d371ff1876d21
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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