3-Bromo-1-phenylpropane-1,2-dione → (5-Methoxy-6,7,8,9-tetrahydroimidazo[1,2-a]quinazolin-2-yl)-phenylmethanone

HRID 371392Notes

Reaction equation

HRID 371392 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[N:6]=[C:5]([NH2:13])[N:4]=1.Br[CH2:15][C:16](=O)[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18]>CCOCC>[CH3:1][O:2][C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[N:6]2[CH:15]=[C:16]([C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:18])[N:13]=[C:5]2[N:4]=1

Participants

4

Reactant 2

HCID 125689113-Bromo-1-phenylpropane-1,2-dioneHCID 133009284-Methoxy-5,6,7,8-tetrahydroquinazolin-2-amine

Product 1

HCID 10402951(5-Methoxy-6,7,8,9-tetrahydroimidazo[1,2-a]quinazolin-2-yl)-phenylmethanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 20 g of 4-methoxy-5,6,7,8-tetrahydro-2-quinazolinamine, 28.6 g of 3-bromo-1-phenyl-propane- 1,2-dione and 400 ml of ether was stirred overnight at room temperature and was filtered. The 29.5 g of 4-methoxy-1-(3-phenyl-2,3-dioxopropyl)-5,6,7,8-tetrahydro-2-quinazolinium bromide were washed with ether and suspended in methanol. The suspension was refluxed for 2 hours and the solution was evaporated to dryness under reduced pressure. The residue was shaken with a mixture of aqueous potassium carbonate and chloroform and the decanted organic phase was washed with water, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue was triturated with ethanol and filtered to obtain 18 g of (5-methoxy-6,7,8,9-tetrahydroimidazo[1,2-a]quinazolin-2-yl-phenylmethanone in the form of pale yellow crystals melting at 234° C.

Workup

  1. filtrationwas filtered
  2. washThe 29.5 g of 4-methoxy-1-(3-phenyl-2,3-dioxopropyl)-5,6,7,8-tetrahydro-2-quinazolinium bromide were washed with ether
  3. temperatureThe suspension was refluxed for 2 hours
  4. customthe solution was evaporated to dryness under reduced pressure
  5. washthe decanted organic phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was triturated with ethanol
  9. filtrationfiltered

Sources & evidence

ORD record
ord-551ed0d5859446bcabfca810110c0562
Source dataset
uspto-grants-1985_07
Patent number
US04532243

Reaction notes

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