Benzene → 3,3'-Diaminobenzophenone

HRID 637549

反応式

HRID 637549 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][C:21]=1Cl)[C:7]([C:9]1[CH:14]=[CH:13][C:12](F)=[C:11]([N+:16]([O-])=O)[CH:10]=1)=[O:8])([O-])=O.C1C=CC=CC=1.[H][H].C(=O)([O-])[O-].[K+].[K+]>[Pd].[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC.Cl>[NH2:1][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:16])[CH:10]=1)=[O:8]

参加物

8

反応物 4

HCID 241BenzeneHCID 11430Potassium CarbonateHCID 229871853,3'-Dinitro-4-chloro-4'-fluoro benzophenoneHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 691453,3'-Diaminobenzophenone収率 104.3%

試薬・触媒・溶媒 3

HCID 21218Trioctylmethylammonium chloride触媒HCID 23938Palladium触媒HCID 313Hydrochloric Acid溶媒

実験手順

To a closed glass vessel equipped with a thermometer and a stirrer, there are added 49 g (0.15 moles) of 3,3'-dinitro-4-chloro-4'-fluoro benzophenone, 1 g of palladium black catalyst and 300 ml of benzene. While the mixture being stirred at 65°-70° C., 20.2 l (0.9 moles) of hydrogen is absorbed therein during about 6 hours. Then, after there are added 180 g (0.45 moles) of 35% aqueous solution of potassium carbonate and 3 g of 90% aqueous solution of trioctylmethyl ammonium chloride (available from Tokyo-Kasei Co.), additional hydrogen, 7.4 l (0.33 moles), is introduced during about 5 hours while the mixture being stirred at 65°-70° C. The mixture at that temperature is filtered to remove the catalyst. Organic phase is separated from the filtrate, added with magnesium sulfate for removing water and then blown with dry hydrochloric gas to saturation. The precipitate thus obtained is filtered, washed with 50 ml of benzene and dried to obtain 33.2 g (yield 77.7%) of 3,3'-diamino benzophenone in the hydrochloric acid salt form. Recrystallization from 20% aqueous isopropyl alcohol gives pure compound, as slightly yellow needle-like crystals. M.P. 265°-267° C. (decomposed).

後処理

  1. customTo a closed glass vessel equipped with a thermometer and a stirrer, there
  2. additionis introduced during about 5 hours while the mixture
  3. stirringbeing stirred at 65°-70° C
  4. filtrationThe mixture at that temperature is filtered
  5. customto remove the catalyst
  6. customOrganic phase is separated from the filtrate
  7. additionadded with magnesium sulfate
  8. customfor removing water
  9. customwith dry hydrochloric gas to saturation
  10. customThe precipitate thus obtained
  11. filtrationis filtered
  12. washwashed with 50 ml of benzene
  13. customdried

出典と根拠

ORDレコード
ord-04b3a5dbfc8645a28e4e89f16160a1f7
出典データセット
uspto-grants-1985_12
特許番号
US04556738

関連ノート

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