2,5-Dichloronitrobenzene → 5-Chloro-1-(4-chloro-2-nitrophenyl)indoline

HRID 34317

反応式

HRID 34317 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.Cl[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].N1C(C)=CC(C)=CC=1C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20])[CH2:6][CH2:5]2

参加物

5

反応物 3

HCID 69772,5-DichloronitrobenzeneHCID 79532,4,6-TrimethylpyridineHCID 1175965-Chloroindoline

生成物 1

HCID 138233265-Chloro-1-(4-chloro-2-nitrophenyl)indoline収率 40%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A stirred solution of 123 g (0.80 mole) of 5-chloroindoline, 134 g (0.70 mole) of 1,4-dichloronitrobenzene and 97 g (0.80 mole) of collidine in 1000 ml of dimethylformamide was heated under nitrogen at 150° C. for 48 hours. The mixture was then cooled, filtered from insolubles, and the solvent was removed in vacuo with warming. The residue was partitioned between 1000 ml of dichloromethane and 500 ml of water. The water layer was removed and the organic phase was washed twice with 2N-hydrochloric acid, once with 2N-sodium hydroxide, once more with water, dried over Na2SO4 and concentrated to an oil weighing 230 g. This was dissolved in 170 ml of methanol and stirred at room temperature and then at 0° C. The resultant crystals were collected, washed well with cold methanol, and dried. This afforded 86.5 g (40% yield) of product, m.p. 130°-133° C. 4 g of 5-chloro-1-(4-chloro-2-nitrophenyl)indoline were recrystallized from methanol in 85% yield (overall yield: 34%); m.p. 133°-135° C.

後処理

  1. temperatureThe mixture was then cooled
  2. filtrationfiltered from insolubles
  3. customthe solvent was removed in vacuo
  4. temperaturewith warming
  5. customThe residue was partitioned between 1000 ml of dichloromethane and 500 ml of water
  6. customThe water layer was removed
  7. washthe organic phase was washed twice with 2N-hydrochloric acid, once with 2N-sodium hydroxide, once more with water
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated to an oil
  10. dissolutionThis was dissolved in 170 ml of methanol
  11. customat 0° C
  12. customThe resultant crystals were collected
  13. washwashed well with cold methanol
  14. customdried

出典と根拠

ORDレコード
ord-8b72b5fd8a894255acc31f52be35beb7
出典データセット
uspto-grants-1988_08
特許番号
US04761411

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