Dimethylformamide → 1-(4-Butylbenzyl)isoquinoline

HRID 2077995ノート

反応式

HRID 2077995 の反応式
CN(C)C=O.[H-].[Na+].[C:8]([CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][N:11]1C(=O)C1C=CC=CC=1)#N.[CH2:28]([C:32]1[CH:39]=[CH:38][C:35](CCl)=[CH:34][CH:33]=1)[CH2:29][CH2:30][CH3:31]>O>[CH2:28]([C:32]1[CH:39]=[CH:38][C:35]([CH2:8][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][N:11]=2)=[CH:34][CH:33]=1)[CH2:29][CH2:30][CH3:31]

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 24758Sodium hydrideHCID 182273Benzene, 1-butyl-4-(chloromethyl)-HCID 2304882-Benzoyl-1,2-dihydro-1-isoquinolinecarbonitrile

生成物 1

HCID 99002251-(4-Butylbenzyl)isoquinoline収率 17.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a dimethylformamide (1.8 ml) solution of 60% sodium hydride (16 mg, 0.40 mmol), a dimethylformamide (3.6 ml) solution of 1-cyano-2-benzoyl-1,2-dihydroisoquinoline (100 mg, 0.38 mmol) synthesized according to the literature of Org. Synth., VI, 115 (1988), and 4-n-butylbenzylchloride (70 mg, 0.38 mmol) was added dropwise under nitrogen atmosphere at −16° C., and was further stirred at room temperature for 30 minutes. Water was added, this was concentrated, and toluene and water were added to this residue. The toluene layer was washed with water, dried over potassium carbonate, and concentrated. To an ethanol (1.6 ml) solution of the residue, 50% aqueous sodium hydroxide solution (0.63 ml) was added, and this was refluxed for 2 hours. After concentration, toluene and water were added. The toluene layer was washed with water, then dried over calcium carbonate, and then concentrated. The residue was purified by silica gel column chromatography to give 18 mg of the aforementioned compound of the formula (Ia).

後処理

  1. concentrationthis was concentrated
  2. additiontoluene and water were added to this residue
  3. washThe toluene layer was washed with water
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated
  6. additionTo an ethanol (1.6 ml) solution of the residue, 50% aqueous sodium hydroxide solution (0.63 ml) was added
  7. temperaturethis was refluxed for 2 hours
  8. concentrationAfter concentration, toluene and water
  9. additionwere added
  10. washThe toluene layer was washed with water
  11. dry with materialdried over calcium carbonate
  12. concentrationconcentrated
  13. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-cbb55e3a1fa643fc8dcceb8c442f3cdf
出典データセット
uspto-grants-2011_04
特許番号
US07928209B2

反応ノート

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