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

HRID 1719940Notes

Reaction equation

HRID 1719940 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]=[C:7]2[NH:14][CH:15]=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])([O-])=O.C1(C)C=CC=CC=1>CN(C)C=O.[Pd].[H][H]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]=[C:7]2[NH:14][CH:15]=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

6

Reactant 2

HCID 1140TolueneHCID 13060485Diethyl[(6-nitro-4-quinazolinylamino)methylene]propanedioate

Product 1

HCID 20266113Diethyl[(6-amino-4-quinazolinylamino)methylene]propanedioateYield 97.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A suspension of diethyl [(6-nitro-4-quinazolinylamino)methylene]propanedioate (2.8 g) in N,N-dimethylformamide (152 ml) was shaken with 10% palladium on carbon (0.93 g) in hydrogen atmosphere at ambient temperature for an hour. After the reaction was completed, the catalyst was removed by filtration and washed with chloroform. The combined filtrate and washing was concentrated under reduced pressure to give a residue, to which was added toluene and concentrated under reduced pressure. This operation was repeated to give crystalline diethyl [(6-amino-4-quinazolinylamino)methylene]propanedioate (2.50 g).

Workup

  1. customthe catalyst was removed by filtration
  2. washwashed with chloroform
  3. washThe combined filtrate and washing
  4. concentrationwas concentrated under reduced pressure
  5. customto give a residue
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-75e9ac969c9646b4b84c07b958786e63
Source dataset
uspto-grants-1985_09
Patent number
US04543356

Reaction notes

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