HCID 135838121, compound → HCID 135838205, compound

HRID 1377060Notes

Reaction equation

HRID 1377060 reaction equation
[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([CH:17]=[CH2:18])[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1>[Pd].C(O)C>[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([CH2:17][CH3:18])[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 135838121HCID 135838121, compound

Product 1

HCID 135838205HCID 135838205, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-amino-9-vinylbenzo[f]quinazolin-1(2H)-one (0.060 g, 0.25 mmol) and 10% palladium on carbon (0.10 g) (Aldrich) in ethanol (200 ml) was shaken under hydrogen (40 psi) for 1 hour and then filtered through celite and concentrated in vacuo. The residue was suspended in ethanol, filtered, and dried at 85° C. under reduced pressure to give 3-amino-9-ethylbenzo[f]-quinazolin-1(2H)-one (0.039 g) as a white solid. 1H NMR (DMSO-d6, 200 MHz) δ: 1.26 (t, J=7 Hz, 3H, CH3), 2.76 (q, J=7 Hz, 2H, CH2), 6.49 (br s, 2H, NH2), 7.21 (d, J=9 Hz, 1H, Ar), 7.31(dd, J=8, 2 Hz, 1H, Ar), 7.77(d, J=8 Hz, Ar), 7.96 (d, J=g Hz, 1H, Ar), 9.47 (s, 1H, Ar), 11.08 (br s, 1H, NH). Mass spectrum (CI--CH4): 240 (M+1, 100%). Anal. Calculated for C14H13N3O0.1H2O: C, 69.75; H, 5.52; N, 17.43. Found: C, 69.79; H, 5.53; N, 17.37.

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated in vacuo
  3. filtrationfiltered
  4. customdried at 85° C. under reduced pressure

Sources & evidence

ORD record
ord-bba50882dc6945038b09cf88a64c8863
Source dataset
uspto-grants-1997_09
Patent number
US05663337

Reaction notes

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