Ethanol → 7-Amino-2-methyl-3-(2-methylphenyl)quinazolin-4(3H)-one

HRID 1974492Notes

Reaction equation

HRID 1974492 reaction equation
[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:10](=[O:19])[C:9]2[C:4](=[CH:5][C:6]([N+:20]([O-])=O)=[CH:7][CH:8]=2)[N:3]=1.[Cl-].[NH4+].C(O)C>[Fe].O>[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:10](=[O:19])[C:9]2[C:4](=[CH:5][C:6]([NH2:20])=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 19101682HCID 19101682, compound

Product 1

HCID 100157107-Amino-2-methyl-3-(2-methylphenyl)quinazolin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a mixture of 2.0 g of iron powder (reduced) and 1.0 g 2-methyl-3-o-tolyl-7-nitro-4-quinazolone (0.0036 mole) in a test tube (8"×1") was added 2 ml of 1 N ammonium chloride and 8 ml ethanol. The mixture was warmed gently in a water bath until the initial vigorous reaction had subsided. The test tube was then heated in the water bath until the solvents had evaporated (about 1 hr). The residue was extracted with four 10 ml portions of benzene, and the extracts were suction-filtered. The filtrate was heated with stirring, and n-hexane was added to cloudiness. The suspension was placed in the refrigerator overnight, and the white crystals were removed by suction-filtration. The yield was 0.9 g (100%), mp 211°-212° C.

Workup

  1. temperatureThe mixture was warmed gently in a water bath until the initial
  2. customvigorous reaction
  3. customhad evaporated (about 1 hr)
  4. extractionThe residue was extracted with four 10 ml portions of benzene
  5. filtrationthe extracts were suction-filtered
  6. temperatureThe filtrate was heated
  7. additionn-hexane was added to cloudiness
  8. customwas placed in the refrigerator overnight
  9. customthe white crystals were removed by suction-filtration

Sources & evidence

ORD record
ord-0ccac9cad7264bca97bb2bb812d52d52
Source dataset
uspto-grants-1994_02
Patent number
US05283247

Reaction notes

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