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

HRID 1910344노트

반응식

HRID 1910344 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 122265145,6-Dihydrobenz(h)quinoline수율 48.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cb896bd978d4455e8dcbf87e755285f5
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08603645B2

반응 노트

불러오는 중…