HCID 135838222, compound → HCID 135838114, compound

HRID 2289235Notes

Reaction equation

HRID 2289235 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 6 200MHz) 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-abe21d37881d459a81c787eefd3a6009
Source dataset
uspto-grants-2000_07
Patent number
US06090941

Reaction notes

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