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

HRID 1030191
ノート
印刷プレビュー

反応式

HRID 1030191 の反応式
[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.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][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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 962WaterHCID 8909Butyl etherHCID 540302836-Methoxy-4-methyl-8-nitro-5-(9-phenylnonoxy) quinoline

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid
溶媒

反応条件

温度
80 °C

実験手順

A stirred mixture of 6-methoxy-4-methyl-8-nitro-5-(9-phenylnonoxy) quinoline (11 g, 0.025 mol), degreased 40 mesh Fe filings (30 g), H2O (100 ml), HOAc (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.

後処理

  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 - Me2CO

出典と根拠

ORDレコード
ord-7bb1a77890fe4ce88797a4ba7145ed82
出典データセット
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05104885

反応ノート

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