Water → 8-Amino-6-methoxy-4-methyl-5-(8-phenyloctoxy) quinoline

HRID 1111393노트

반응식

HRID 1111393 반응식
[CH3:1][O:2][C:3]1[C:4]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:5]2[C:10](=[C:11]([N+:13]([O-])=O)[CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH3:16].O.O(CCCC)CCCC>[Fe].CC(O)=O>[NH2:13][C:11]1[CH:12]=[C:3]([O:2][CH3:1])[C:4]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[C:6]2[CH3:16]

참가 물질

6

반응물 3

HCID 962WaterHCID 8909Butyl etherHCID 543454366-Methoxy-4-methyl-8-nitro-5-(8-phenyloctoxy) quinoline

생성물 1

HCID 543948298-Amino-6-methoxy-4-methyl-5-(8-phenyloctoxy) quinoline수율 61.1%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

실험 절차

A stirred mixture of 6-methoxy-4-methyl-8-nitro-5-(8-phenyloctoxy) quinoline (2.1 g, 0.005 mol), degreased 40 mesh Fe filings (5 g), H2O (20 ml), HOAc (4 ml) and n-Bu2O (4 ml) was heated at 80° C. to 1.5 h, cooled and filtered. The solid was thoroughly extracted with Et2O and the filtered extract was dried (Na2SO4), treated with carbon and concentrated to an oil. Trituration with pet ether gave 1.2 g (61%) of 8-amino-6-methoxy-4-methyl-5-(8-phenyloctoxy) quinoline as yellow-green solid, mp 33°-34° C. Crystallization from pet ether (Darco) gave the analytical sample as yellow green crystals, mp 39°-40° C.

후처리

  1. temperaturewas heated at 80° C. to 1.5 h
  2. temperaturecooled
  3. filtrationfiltered
  4. extractionThe solid was thoroughly extracted with Et2O
  5. extractionthe filtered extract
  6. dry with materialwas dried (Na2SO4)
  7. additiontreated with carbon
  8. concentrationconcentrated to an oil

출처 및 근거

ORD 기록
ord-e1e3b54f1b014628bc2b82556250e010
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04980360

반응 노트

불러오는 중…