p-Toluidine → HCID 14551372, compound

HRID 275365Notes

Reaction equation

HRID 275365 reaction equation
NC1C=CC(C)=CC=1.N([O-])=O.[Na+].[F:13][C:14]1[CH:28]=[CH:27][C:17]([CH2:18][CH:19](C(=O)C)[C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=1.[OH-:29].[K+]>Cl.O.C(O)C>[O:29]=[C:19]([CH2:18][C:17]1[CH:27]=[CH:28][C:14]([F:13])=[CH:15][CH:16]=1)[C:20]([O:22][CH3:23])=[O:21]

Participants

8

Reactant 4

HCID 7813p-ToluidineHCID 14797Potassium HydroxideHCID 2758966HCID 2758966, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14551372HCID 14551372, compoundYield 150.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of p-toluidine (119.4 g) in conc. aqueous HCl (575 ml) was added a solution of NaNO2 (84.6 g) in water (500 ml) at 0°-5° C. during 1.5 h. The reaction mixture was added in one portion to a mixture of methyl 2-(4-fluorobenzyl)-3-oxobutanoate (250 g), KOH (220 g), water (0.5 l), ethanol (1.25 l) and ice (2 kg) under stirring. After reaction for 2 h at room temperature the reaction mixture was extracted with diethyl ether (2×2 l). The combined organic phases were washed with water (3 l) and dried (Na2SO4). Evaporation of the solvents afforded the crude 4-tolylhydrazone of methyl 2-oxo-3-(4-fluorophenyl)-propanoate (330 g), which was used without further purification.

Workup

  1. customAfter reaction for 2 h at room temperature the reaction mixture
  2. extractionwas extracted with diethyl ether (2×2 l)
  3. washThe combined organic phases were washed with water (3 l)
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvents

Sources & evidence

ORD record
ord-60debbb6061d49e9befa068fddad5e12
Source dataset
uspto-grants-1995_02
Patent number
US05393761

Reaction notes

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