Toluene → HCID 19867308, compound

HRID 1198837Notes

Reaction equation

HRID 1198837 reaction equation
Cl.[NH2:2]O.[CH2:4]([C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C@H:22]3[CH2:27][CH2:26][C@H:25]([CH:28]=O)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[N:14][CH:15]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C1(C)C=CC=CC=1>N1C=CC=CC=1>[CH2:4]([C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][CH:25]([C:28]#[N:2])[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[N:14][CH:15]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 1140TolueneHCID 443297Hydroxyamine hydrochlorideHCID 178442346HCID 178442346, compound

Product 1

HCID 19867308HCID 19867308, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 0.7 g of hydroxylamine hydrochloride in 1.58 g of pyridine is treated with 3.41 g of 5-hexyl-2-[p-(trans-4-formylcyclohexyl)phenyl]pyridine and stirred at room temperature for 5 minutes. The reaction mixture is then treated with 20 ml of toluene and heated to reflux for 4 hours under water separation. The cooled reaction mixture is filtered. The filtrate is diluted with diethyl ether, washed several times with water and dried over magnesium sulphate. After evaporation there is obtained 5-hexyl-2-[p- -(4-cyanocyclohexyl)phenyl]pyridine as a cis/trans mixture.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours under water
  3. customseparation
  4. customThe cooled reaction mixture
  5. filtrationis filtered
  6. additionThe filtrate is diluted with diethyl ether
  7. washwashed several times with water
  8. dry with materialdried over magnesium sulphate
  9. customAfter evaporation

Sources & evidence

ORD record
ord-79bf30b521d94affb22f44e262355653
Source dataset
uspto-grants-1990_02
Patent number
US04898455

Reaction notes

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