Pyridine → HCID 178447943, compound

HRID 542699Notes

Reaction equation

HRID 542699 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21](Br)=[CH:20][C:19]=3[F:25])=[CH:14][CH:13]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[C:26](C#N)#[N:27].N1C=CC=CC=1.CN1CCCC1=O>Cl>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:26]#[N:27])=[CH:20][C:19]=3[F:25])=[CH:14][CH:13]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 1049PyridineHCID 9999CyanogenHCID 13387N-methyl-2-pyrrolidoneHCID 178447941HCID 178447941, compound

Product 1

HCID 178447943HCID 178447943, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 38.4 g of 1-(trans-4-n-propylcyclohexyl)-2-(4'-bromo-2'-fluorobiphenyl-4-yl)-ethane (M.p. 61.1°, C.p. 114.7°), 10 g of Cu2 (CN)2, 120 ml of pyridine and 60 ml of N-methylpyrrolidone is heated at 160° for 2 hours. The mixture is cooled, a solution of 120 g of FeCl3.6H2O in 600 ml of 20% hydrochloric acid is added and the mixture is warmed at 70° for 1.5 hours, with stirring, and worked up in the customary manner to give 1-(trans-4-n-propylcyclohexyl)-2-(4'-cyano-2'-fluorobiphenyl-4-yl)-ethane, M.p. 89.4°, C.p. 168.4°.

Workup

  1. temperatureis heated at 160° for 2 hours
  2. temperatureThe mixture is cooled
  3. temperaturethe mixture is warmed at 70° for 1.5 hours

Sources & evidence

ORD record
ord-c6bcbd065a5f440580a9dbaeae069d95
Source dataset
uspto-grants-1987_04
Patent number
US04659502

Reaction notes

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