HCID 11463573, compound → 6-Methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

HRID 1791518Notes

Reaction equation

HRID 1791518 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[N:9]=[CH:8][N:7]=[C:6]2[O:23]C1C=CC=CC=1>Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[N:9]=[CH:8][NH:7][C:6]2=[O:23]

Participants

3

Reactant 1

HCID 11463573HCID 11463573, compound

Product 1

HCID 1354371166-Methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-oneYield 89.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

6-Methoxy-7-(3-morpholinopropoxy)-4-phenoxyquinazoline (33.08 g, 84 mmol) was dissolved in 6M aqueous hydrochloric acid (800 ml) and heated at reflux for 1.5 hours. The reaction mixture was decanted and concentrated to 250 ml then basified (pH9) with saturated aqueous sodium hydrogen carbonate solution. The aqueous layer was extracted with dichloromethane (4×400 ml), the organic layer was separated and filtered through phase separating paper. The solid was triturated with ethyl acetate to give 6-methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one (23.9 g, 89%) as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 hours
  3. customThe reaction mixture was decanted
  4. concentrationconcentrated to 250 ml
  5. extractionThe aqueous layer was extracted with dichloromethane (4×400 ml)
  6. customthe organic layer was separated
  7. filtrationfiltered through phase
  8. customseparating paper
  9. customThe solid was triturated with ethyl acetate

Sources & evidence

ORD record
ord-abe597ff8efa41fdb57f768e0a03584f
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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