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

HRID 735243노트

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HRID 735243 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ab5b92b023824ad5b46be79fddc8883f
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592457B2

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