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

HRID 735243ノート

反応式

HRID 735243 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ab5b92b023824ad5b46be79fddc8883f
出典データセット
uspto-grants-2009_09
特許番号
US07592457B2

反応ノート

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