Boron tribromide → 5-(4-Hydroxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile

HRID 11322ノート

反応式

HRID 11322 の反応式
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([C:17]#[N:18])[C:12](=[O:16])[NH:13][C:14]=2[CH3:15])=[CH:5][CH:4]=1.B(Br)(Br)Br.[Cl-].[NH4+]>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]([C:17]#[N:18])[C:12](=[O:16])[NH:13][C:14]=2[CH3:15])=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 133747585-(4-Methoxyphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

生成物 1

HCID 133747555-(4-Hydroxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile収率 46%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of 5-(4-Methoxy-phenyl)-6-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (5, 10.0 g, 41.6 mmol) in dichloromethane (200 mL) was added dropwise at 0° C. a solution of boron tribromide (11.8 mL, 125 mmol) in DCM (125 mL). The reaction mixture was stirred for 6 h at ambient temperature, poured into a mixture of ice and saturated ammonium chloride solution (100 mL) and stirred for 1 h at room temperature. The formed precipitate was filtered off, rinsed with water and re-dissolved in aqueous sodium hydroxide (2 N, 400 mL). The aqueous solution was washed with ethyl acetate (100 mL), acidified to pH 4 with aqueous hydrochloric acid (2 N) and extracted with ethyl acetate (3×200 mL). The combined organic phases were washed with brine (2×200 mL), dried (MgSO4) and evaporated to dryness to give 5-(4-hydroxy-phenyl)-6-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (6) as a yellow solid (3.25 g, 46% yield, 92% pure by LC-MS and 1H NMR), 1H NMR (400 MHz; CDCl3): δ 7.70 (s, 1H); 7.13 (m, 2H); 6.68 (m, 2H); 1.71 (s, 3H).

後処理

  1. stirringstirred for 1 h at room temperature
  2. filtrationThe formed precipitate was filtered off
  3. washrinsed with water
  4. dissolutionre-dissolved in aqueous sodium hydroxide (2 N, 400 mL)
  5. washThe aqueous solution was washed with ethyl acetate (100 mL)
  6. extractionextracted with ethyl acetate (3×200 mL)
  7. washThe combined organic phases were washed with brine (2×200 mL)
  8. dry with materialdried (MgSO4)
  9. customevaporated to dryness

出典と根拠

ORDレコード
ord-2b7de4ef98f44debbfc0e293c0fd87ff
出典データセット
uspto-grants-2006_08
特許番号
US07098211B2

反応ノート

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