Hydrochloric Acid → 2-Biphenyl-4-yl-1H-indole

HRID 1438864Notes

Reaction equation

HRID 1438864 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=O.Cl>O>[C:18]1([C:15]2[CH:14]=[CH:13][C:12]([C:10]3[NH:1][C:2]4[C:7]([CH:9]=3)=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:17][CH:16]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 69463Ethanone, 1-(1,1'-biphenyl)-4-yl-2-chloro-

Product 1

HCID 3929042-Biphenyl-4-yl-1H-indoleYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 372 g (4 mols) of aniline and 230 g (1 mol) of ω-chloroparaphenyl-acetophenone was refluxed for 105 minutes. After cooling to about 50°-80° C, the mixture was poured into iced-water containing 50 ml of concentrated hydrochloric acid to give a precipitate which was filtered out, washed with water, dried and then recrystallized from N,N-dimethylformamide. The pure substance was then filtered out and washed with ethanol to give 67.2 g of 2-(4'-phenyl-phenyl)-indole.

Workup

  1. temperaturewas refluxed for 105 minutes
  2. temperatureAfter cooling to about 50°-80° C
  3. customto give a precipitate which
  4. filtrationwas filtered out
  5. washwashed with water
  6. customdried
  7. customrecrystallized from N,N-dimethylformamide
  8. filtrationThe pure substance was then filtered out
  9. washwashed with ethanol

Sources & evidence

ORD record
ord-29a102cee2da4c8ca3e1ac3bf93e7bb5
Source dataset
uspto-grants-1977_11
Patent number
US04057530

Reaction notes

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