Acetic Acid → 4-(6,7-Dimethoxyquinazolin-4-yloxy)benzene-1,2-diamine

HRID 491672Notes

Reaction equation

HRID 491672 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([N+:23]([O-])=O)[CH:17]=1.C(O)(=O)C>CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]([NH2:23])[C:19]([NH2:22])=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 177554014-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-nitroaniline

Product 1

HCID 177555094-(6,7-Dimethoxyquinazolin-4-yloxy)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(6,7-Dimethoxyquinazolin-4-yloxy)-2-nitro-phenylamine (Step A, 1 g, 2.9 mmol) was dissolved in EtOH (200 mL) and glacial acetic acid (10 mL) and placed under nitrogen. Pd/C was added, the reaction mixture blanketed with H2, the mixture was shaken under H2 for 18 h at 55 psi. The catalyst was removed by filtration through Celite® and the solution was concentrated in vacuo. The residue was dissolved in MeOH/H2O and NH4OH was added to adjust to PH 10, and the solvent evaporated. Purification of the residue by column chromatography using a gradient of 0-100% of a 90:10:1 (CH2Cl2:MeOH: NH4OH) afforded the title compound as a orange solid. MS(MH+)=N/A; Calc'd 312.32 for C16H16N4O3.

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. concentrationthe solution was concentrated in vacuo
  3. dissolutionThe residue was dissolved in MeOH/H2O
  4. additionNH4OH was added
  5. customthe solvent evaporated
  6. customPurification of the residue by column chromatography

Sources & evidence

ORD record
ord-106f2840ef994ae8bade81d578983ce9
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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