Hydrochloric Acid → 5,7-dichloro-3-(4-hydroxy-phenyl)-3-methyl-1H-quinoline-2,4-dione

HRID 735243Notes

Reaction equation

HRID 735243 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:15]1[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=1)([CH3:14])[C:6](=[O:13])[NH:7]2.B(Br)(Br)Br.Cl>ClCCl>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)([CH3:14])[C:6](=[O:13])[NH:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 116746945,7-dichloro-3-(4-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione

Product 1

HCID 115952095,7-dichloro-3-(4-hydroxy-phenyl)-3-methyl-1H-quinoline-2,4-dioneYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a pre-cooled (−78° C.) solution of 5,7-dichloro-3-(4-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione (0.23 g, 0.77 mmol) in dichloromethane (5.0 mL) was added BBr3 (1.40 mL, 1.0 M dichloromethane solution) by syringe. The reaction was conducted for 20 hours at room temperature and qeunched by carefully addition of 1N HCl aqueous solution. Resultant was extracted with ethyl acetate (50 mL×2), washed with brine (50 mL) and water (50 mL×2), and dried over magnesium sulfate. After concentration of the organic phase, the residue was subjected to purify by a flash column chromatography (n-hexane:EtOAc=5:1) to give a pure objective compound (0.19 g, 83%) as yellow solid: 1H NMR (300 MHz, CD3OD) δ 1.58 (s, 3H, CH3), 6.65-6.71 (m, 2H, ArH), 6.91 (d, J=1.9 Hz, 1H, ArH), 6.94-6.99 (m, 2H, ArH), 7.03-7.06 (m, 1H, ArH); m.p. 222-223° C.; MS(EI) m/e 335 [M+], 188, 140, 120; HRMS m/e cacld. for C16H11NO3Cl2 335.0116, found 335.0112.

Workup

  1. extractionResultant was extracted with ethyl acetate (50 mL×2)
  2. washwashed with brine (50 mL) and water (50 mL×2)
  3. dry with materialdried over magnesium sulfate
  4. customto purify by a flash column chromatography (n-hexane:EtOAc=5:1)

Sources & evidence

ORD record
ord-ab5b92b023824ad5b46be79fddc8883f
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

Loading…