Ethanol → 4-Cyclohexylphenylhydrazine hydrochloride

HRID 1655827Notes

Reaction equation

HRID 1655827 reaction equation
[CH:1]1([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C.[N:17]([O-])=O.[Na+].O.O.[Sn](Cl)[Cl:24]>Cl.O>[ClH:24].[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH:11][NH2:17])=[CH:12][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 807644-CyclohexylbenzenamineHCID 23668193Sodium Nitrite

Product 1

HCID 187022954-Cyclohexylphenylhydrazine hydrochlorideYield 66.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

To a slurry a 4-cyclohexylaniline (350.6 g) and ethanol (330 ml) in 30% HCl (1470 ml) was added a solution of sodium nitrite (151.8 g) in water (735 ml), while maintaining the temperature between -8 to -2° C. The reaction was stirred for an additional four hours at -2 to 10° C. A solution of tin (II) chloride dihydrate (1353.8 g) in 30% HCl (1470 ml) was added slowly, and the resulting white suspension was cooled overnight. The crude product was collected by vacuum filtration and washed with 1 N hydrochloric acid, and ether. Recrystallization in 6 L of methanol gave 300 g of the desired product as fine long needles, m.p. 251-254° C.

Workup

  1. temperaturethe resulting white suspension was cooled overnight
  2. filtrationThe crude product was collected by vacuum filtration
  3. washwashed with 1 N hydrochloric acid, and ether
  4. customRecrystallization in 6 L of methanol

Sources & evidence

ORD record
ord-94d549ad56f145d1901cfdbef35efb10
Source dataset
uspto-grants-1993_10
Patent number
US05252426

Reaction notes

Loading…