HCID 135838222, compound → HCID 135838114, compound

HRID 1883993Notes

Reaction equation

HRID 1883993 reaction equation
[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[C:7]=3[CH2:6][CH2:5][C:4]=2[N:3]=1>[Pd].COCCOCCOC>[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 135838222HCID 135838222, compound

Product 1

HCID 135838114HCID 135838114, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8150DiglymeSolvent

Procedure

A mixture of 3-amino-5,6-dihydro-7,9-dimethylbenzo[f]quinazolin-1(2H)one (0.25 g, 1.04 mmole) and 10% palladium on carbon (0.5 g) in diglyme (25 ml) was vigorously stirred and refluxed under a nitrogen atmosphere for 2.5 hours, and then filtered while still hot through a bed of celite. Diglyme was removed from the filtrate under reduced pressure, and the residue was triturated with hot methanol, filtered, washed with methanol and ether, and dried to give 3-amino-7,9-di-methylbenzo[f]quinazolin-1(2H)-one as an off-white solid. (0.14 g, 55%) 1H NMR (DMSO-d6, 200 MHz) δ: 2.43 (s, 3H, CH3); 2.60 (s, 3H, CH3); 6.48 (s, 2H, NH2); 7.14 (s, 1H, Ar); 7.25 (d, J=9.2 Hz, 1H, Ar); 8.11 (d, J=9.1 Hz, 1H, Ar); 9.38 (s, 1H, Ar); 11.07 (s, 1H, NH).

Workup

  1. temperaturerefluxed under a nitrogen atmosphere for 2.5 hours
  2. filtrationfiltered while still hot through a bed of celite
  3. customDiglyme was removed from the filtrate under reduced pressure
  4. customthe residue was triturated with hot methanol
  5. filtrationfiltered
  6. washwashed with methanol and ether
  7. customdried

Sources & evidence

ORD record
ord-4a0203a7923748c09c9250b313944820
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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