Hydrazine hydrate (1:1) → HCID 20352827, compound

HRID 371988Notes

Reaction equation

HRID 371988 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([N:13]([CH3:21])[CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[O:12])=[CH:6][CH:5]=1)([O-])=O.O.NN>[Pd].C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([N:13]([CH3:21])[CH2:14][C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20352819HCID 20352819, compound

Product 1

HCID 20352827HCID 20352827, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a mixture of 5.72 gms. (0.02 mole) of 1-(p-nitrophenyl)-3-methyl-3-(4-pyridylmethyl)urea (see U.S. Pat. No. 3,700,678), 200 ml. of ethanol and 65 ml. of hydrazine hydrate there is added with stirring 0.5 gms. of 5 percent palladium-on-carbon in 50 ml. of ethanol. The resulting mixture is allowed to stand overnight at room temperature and then is refluxed for 2 to 3 hours. The hot reaction mixture is then filtered and the filtrate evaporated to remove solvent. The residue is 1-(p-aminophenyl)-3-methyl-3-(4-pyridylmethyl)urea.

Workup

  1. additionTo a mixture of 5.72 gms
  2. temperatureis refluxed for 2 to 3 hours
  3. filtrationThe hot reaction mixture is then filtered
  4. customthe filtrate evaporated
  5. customto remove solvent

Sources & evidence

ORD record
ord-a814468f38fc4381aaf6568fa88fb0c6
Source dataset
uspto-grants-1978_05
Patent number
US04088766

Reaction notes

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