HCID 20339473, compound → HCID 20339606, compound

HRID 1395546Notes

Reaction equation

HRID 1395546 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([N:5]([CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][N:7]=1)=[O:4].[H][H]>C(O)C.[Pd]>[CH3:1][N:2]([CH3:20])[C:3]([N:5]([CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][N:7]=1)=[O:4]

Participants

5

Reactant 2

HCID 20339473HCID 20339473, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20339606HCID 20339606, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N,N-Dimethyl-N'-(2-dimethylaminoethyl)-N'-(5-nitro-2-pyridyl)urea (9.68 g., 0.034 mole) is dissolved in absolute ethanol (50 ml.) containing 10% palladium-on-carbon and is hydrogenated at an initial 42 psi of hydrogen at ambient temperature for two hours. The reaction mixture is flushed with nitrogen and then is filtered under nitrogen. The filtrate is concentrated in vacuo on a steam bath to give a nearly colorless oil (8.05 g.) which partially solidifies on standing. Crystallization from acetonitrile yields 5.19 g. of the title compound, m.p. 118°-119° C.

Workup

  1. customat ambient temperature
  2. customfor two hours
  3. customThe reaction mixture is flushed with nitrogen
  4. filtrationis filtered under nitrogen
  5. concentrationThe filtrate is concentrated in vacuo on a steam bath
  6. customto give a nearly colorless oil (8.05 g.) which
  7. customCrystallization from acetonitrile
  8. customyields 5.19 g

Sources & evidence

ORD record
ord-a1b4b570dc2c4fb89aa21c196c9dc799
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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