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(4-Chlorophenyl){2-[(3-nitropyridin-2-yl)amino]phenyl}methanone → {2-[(3-Aminopyridin-2-yl)amino]phenyl}(4-chlorophenyl)methanone

HRID 1633367
ノート
印刷プレビュー

反応式

HRID 1633367 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17]2[C:22]([N+:23]([O-])=O)=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:9])=[CH:4][CH:3]=1.C(OCC)(=O)C.CO.C(O)(=O)C.O>O.[Cl-].[Cl-].[Cl-].[Ti+3]>[NH2:23][C:22]1[C:17]([NH:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:9])=[N:18][CH:19]=[CH:20][CH:21]=1
参加物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 13388387(4-Chlorophenyl){2-[(3-nitropyridin-2-yl)amino]phenyl}methanoneHCID 21584119Ethylacetate methanolHCID 21899381Acetic acid--water (1/1)

生成物 1

HCID 13388390{2-[(3-Aminopyridin-2-yl)amino]phenyl}(4-chlorophenyl)methanone収率 59.4%

試薬・触媒・溶媒 2

HCID 10313229titanium(III) trichloride触媒2 回
HCID 962Water溶媒2 回

実験手順

Under an atmosphere of nitrogen, 29 g (0.187 mole) of titanium trichloride was added portionwise (cautiously; in hood) to 200 g of ice and the resulting solution was diluted to 250 ml volume with water. This was added, all at once, at 30° C. to a stirred solution of 11.0 g (0.0312 mole) of (4-chlorophenyl)[2-[(3-nitro-2-pyridinyl)amino]phenyl]methanone, 300 ml of ethyl acetate: methanol (1:1), 100 ml of acetic acid: water (1:1) and 20 ml more solution of titanium trichloride. The reaction mixture was stirred for 20 min then diluted with one liter of water and filtered. The filter cake was washed with water and then partitioned between 200 ml of methylene chloride and 75 ml of 10% aqueous sodium hydroxide solution. The methylene chloride layer was washed with 75 ml of water, dried over sodium sulfate and concentrated in vacuo. The residue (7 g) was recrystallized from ethyl acetate-isopropyl ether to give 6.0 g of gold solid, m.p. 145°-146° C.

後処理

  1. additionThis was added
  2. customat 30° C.
  3. filtrationfiltered
  4. washThe filter cake was washed with water
  5. custompartitioned between 200 ml of methylene chloride and 75 ml of 10% aqueous sodium hydroxide solution
  6. washThe methylene chloride layer was washed with 75 ml of water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue (7 g) was recrystallized from ethyl acetate-isopropyl ether

出典と根拠

ORDレコード
ord-f373c202c98646ce95cb35c3fd769ce8
出典データセット
uspto-grants-1984_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04480100

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート