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Butyl ether → 8-Amino-6-methoxy-4-methyl-5-(9-phenylnonoxy) quinoline

HRID 1111395
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인쇄 미리보기

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HRID 1111395 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][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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(CCCC)CCCC>[Fe].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][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[C:6]2[CH3:16]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 8909Butyl etherHCID 540302836-Methoxy-4-methyl-8-nitro-5-(9-phenylnonoxy) quinoline

생성물 1

HCID 541929178-Amino-6-methoxy-4-methyl-5-(9-phenylnonoxy) quinoline수율 64%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A stirred mixture of 6-methoxy-4-methyl-8nitro-5-(9-phenylnonoxy) quinoline (11 g, 0.025 mol), degreased 40 mesh Fe filings (30 g), H2O (100 ml), HOA c (20 ml) and n-Bu2O (20 ml) was heated at 80° C. for 2 h, cooled and filtered. The solid residue and the filtrate were thoroughly extracted with warm Et2O and the combined extracts were dried (Na2SO4), treated with Darco, and concentrated. The resulting solid was dissolved in pet ether (Darco) and cooled in dry ice--Me2CO to give 6.5 g (64) of 8-amino-6-methoxy-4-methyl-5-(9-phenylnonoxy) quinoline as pale yellow crystals, mp 32°-32.5° C.

후처리

  1. temperaturecooled
  2. filtrationfiltered
  3. extractionThe solid residue and the filtrate were thoroughly extracted with warm Et2O
  4. dry with materialthe combined extracts were dried (Na2SO4)
  5. additiontreated with Darco
  6. concentrationconcentrated
  7. dissolutionThe resulting solid was dissolved in pet ether (Darco)
  8. temperaturecooled in dry ice

출처 및 근거

ORD 기록
ord-587fb22c925d4085888c5f2894b92867
출처 데이터셋
uspto-grants-1990_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04980360

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