Benzene → Diethyl[(6-amino-4-quinazolinylamino)methylene]propanedioate

HRID 1719950Notes

Reaction equation

HRID 1719950 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5](=[CH:11][NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N+:23]([O-])=O)[CH:21]=2)[N:16]=[CH:15][N:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C1C=CC=CC=1>CN(C)C=O.[Pd].[H][H]>[CH2:1]([O:3][C:4](=[O:26])[C:5](=[CH:11][NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([NH2:23])[CH:21]=2)[N:16]=[CH:15][N:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

6

Reactant 2

HCID 241BenzeneHCID 13060485Diethyl[(6-nitro-4-quinazolinylamino)methylene]propanedioate

Product 1

HCID 20266113Diethyl[(6-amino-4-quinazolinylamino)methylene]propanedioate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A solution of diethyl[(6-nitro-4-quinazolinylamino)methylene]propanedioate (10.8 g) in N,N-dimethylformamide (325 ml) was shaken with 10% palladium on carbon (3.6 g) in hydrogen atmosphere at ambient temperature. After the absorption of hydrogen was finished, the catalyst was removed by filtration. The filtrate was concentrated under reduced pressure to give a residue, to which was added benzene. The mixture was concentrated under reduced pressure to give crude crystals of diethyl[(6-amino-4-quinazolinylamino)methylene]propanedioate.

Workup

  1. customAfter the absorption of hydrogen
  2. customthe catalyst was removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give a residue
  5. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bd93e36d85ad42658dad8432674d1ed7
Source dataset
uspto-grants-1985_09
Patent number
US04543356

Reaction notes

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