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

HRID 2096093ノート

反応式

HRID 2096093 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-3424cbd39dd648829857e3605aaef3d0
出典データセット
uspto-grants-2013_05
特許番号
US08449990B2

反応ノート

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