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

HRID 354869Notes

Reaction equation

HRID 354869 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-7ff08e1c5cd44695a61035c57d6381d4
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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