p-Aminoacetophenone → HCID 135622204, compound

HRID 1377088Notes

Reaction equation

HRID 1377088 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:15]=[CH:14][C:13]3[N:12]=[C:11]([CH3:16])[NH:10][C:9](=[O:17])[C:8]=3[C:7]=2[CH:18]=1.[CH3:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1)=[O:21].C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:20]([C:22]1[CH:27]=[CH:26][C:25]([NH:28][CH2:2][C:3]2[CH:4]=[CH:5][C:6]3[CH:15]=[CH:14][C:13]4[N:12]=[C:11]([CH3:16])[NH:10][C:9](=[O:17])[C:8]=4[C:7]=3[CH:18]=2)=[CH:24][CH:23]=1)(=[O:21])[CH3:19]

Participants

5

Reactant 3

HCID 7468p-AminoacetophenoneHCID 516892Sodium BicarbonateHCID 1354009769-bromomethyl-3-methylbenzo[f]quinazolin-1(2H)-one

Product 1

HCID 135622204HCID 135622204, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

9-Bromomethyl-3-methyl benzo[f]quinazolin-1(2H)-one (1 g, 3.3 mmole) and 4-aminoacetophenone (0.89 g, 6.6 mmole) (Aldrich) were dissolved in dimethylformamide (15 ml). The solution was stirred under nitrogen at 100° C. for 30 min. Sodium bicarbonate (0.55 g, 6.6 mmole) was added and stirring was continued for a further 30 min. Dimethylformamide was removed in vacuo, the residue triturated with water and the solid collected by filtration. The dried solid was subjected to chromatography on silica (methanol/methylene chloride (1:19)). Fractions containing product were concentrated until solid began to precipitate. The solution was chilled at 5° C. for 12 hours, then the solid filtered off and dried under high vacuum to yield the title compound (0.48 g,41%). Mp>235° C. 1H NMR (DMSO-d6, 300 MHz) δ: 2.37 (s, 3H, CH3); 2.43 (s, 3H, CH3); 4.59 (d, J=6 Hz, 2H, CH2); 6.65 (d, J=9 Hz, 2H, Ar); 7.37 (t, J=6 Hz, 1H, ArNH); 7.59 (d, J=9 Hz, 1H, Ar); 7.61 (dd, J=8, 2 Hz, 1H, Ar); 7.69 (d, J=9 Hz, 2H, Ar); 8.00 (d, J=8 Hz, 1H, Ar); 8.21 (d, J=9 Hz, 1H, Ar); 9.85 (s, 1H, Ar); 12.52 (s, 1H, NH). Anal. Calculated for C22H19N3O2.1/2 H2O: C,72.11; H,5.50; N,11.47. Found: C,72.26; H,5.46; N,11.35.

Workup

  1. stirringstirring
  2. waitwas continued for a further 30 min
  3. customDimethylformamide was removed in vacuo
  4. customthe residue triturated with water
  5. filtrationthe solid collected by filtration
  6. additionFractions containing product
  7. concentrationwere concentrated until solid
  8. customto precipitate
  9. temperatureThe solution was chilled at 5° C. for 12 hours
  10. filtrationthe solid filtered off
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-501db40f632f46acbc8dfb65ce49786f
Source dataset
uspto-grants-1997_09
Patent number
US05663337

Reaction notes

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