Hydroxyamine hydrochloride → 5,6-Dihydrobenz(h)quinoline

HRID 2262367ノート

反応式

HRID 2262367 の反応式
Cl.[NH2:2]O.C(O[CH:7]1[CH:16](C)[CH2:15][C:14]2[CH2:13][CH2:12][C:11]3[CH:18]=[CH:19][CH:20]=[CH:21][C:10]=3[C:9]=2O1)C>C(#N)C>[N:2]1[C:9]2[C:10]3[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=3[CH2:12][CH2:13][C:14]=2[CH:15]=[CH:16][CH:7]=1

参加物

4

反応物 2

HCID 443297Hydroxyamine hydrochlorideHCID 592948342-Ethoxy-3-methyl-3,4,5,6-tetrahydrobenzo[h]chromene

生成物 1

HCID 122265145,6-Dihydrobenz(h)quinoline収率 48.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a suspension of hydroxylamine hydrochloride (46.1 g, 0.663 mol) in 1070 mL of acetonitrile was added 2-ethoxy-3-methyl-3,4,5,6-tetrahydrobenzo[h]chromene (140 g, 0.265 mol) from step two. The reaction mixture was heated at reflux under nitrogen with stirring for 16 h. Evaporation of the acetonitrile, followed by vacuum distillation of the product yielded 34.5 g of a crude product that was further purified by silica gel chromatography with 5/95 ethyl acetate/hexane as the eluent, yielding 23.2 g (45%) of 5,6-dihydrobenzo[h]quinoline as a yellow liquid.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under nitrogen
  3. customEvaporation of the acetonitrile
  4. distillationfollowed by vacuum distillation of the product
  5. customyielded 34.5 g of a crude product that
  6. customwas further purified by silica gel chromatography with 5/95 ethyl acetate/hexane as the eluent

出典と根拠

ORDレコード
ord-912d5e6702744221b08e00579fc54e10
出典データセット
uspto-grants-2010_12
特許番号
US07851072B2

反応ノート

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