3-(4-sec-butylphenyl)-2-(3,4-dinitrophenyl)quinazolin-4(3H)-one → 3-(4-sec-butylphenyl)-2-(3,4-diaminophenyl)quinazolin-4(3H)-one

HRID 1846366Notes

Reaction equation

HRID 1846366 reaction equation
[CH:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[C:24]([N+:31]([O-])=O)[CH:23]=2)=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2]>CCO>[CH:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:22]2[CH:27]=[CH:26][C:25]([NH2:28])=[C:24]([NH2:31])[CH:23]=2)=[CH:9][CH:10]=1)([CH2:3][CH3:4])[CH3:2]

Participants

3

Reactant 1

HCID 866598193-(4-sec-butylphenyl)-2-(3,4-dinitrophenyl)quinazolin-4(3H)-one

Product 1

HCID 866598203-(4-sec-butylphenyl)-2-(3,4-diaminophenyl)quinazolin-4(3H)-oneYield 62.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-sec-butylphenyl)-2-(3,4-dinitrophenyl)quinazolin-4(3H)-one (0.240 g, 0.54 mmol) was dissolved in EtOH (20 mL) and flushed with N2 for 15 minutes. Pd/C (0.025 g, 10 wt %) was added, and stirred under 1 atmosphere of H2 overnight. After flushing with N2, the mixture was filtered through diatomaceous earth. The filtrate was concentrated and purified by flash chromatography on silica gel, eluting with 0% to 10% MeOH in EtOAc, to afford 3-(4-sec-butylphenyl)-2-(3,4-diaminophenyl)quinazolin-4(3H)-one (0.130 g, 62%).

Workup

  1. customflushed with N2 for 15 minutes
  2. additionPd/C (0.025 g, 10 wt %) was added
  3. customAfter flushing with N2
  4. filtrationthe mixture was filtered through diatomaceous earth
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash chromatography on silica gel
  7. washeluting with 0% to 10% MeOH in EtOAc

Sources & evidence

ORD record
ord-77c01d0d43424793bc47aecf07e091a2
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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