Hydrochloric Acid → HCID 135589779, compound

HRID 384821Notes

Reaction equation

HRID 384821 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][Cl:17])[N:9]=[CH:8][NH:7][C:6]2=[O:18].Cl.[CH3:20][OH:21]>CC(C)=O>[ClH:17].[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:7]1[CH2:6][CH2:5][O:21][CH2:20][CH2:8]1)[N:9]=[CH:8][NH:7][C:6]2=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1355897776-Methoxy-7-(3-chloropropoxy)quinazolin-4-one

Product 1

HCID 135589779HCID 135589779, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 1,000 mL volume glass vessel equipped with a stirrer, a thermometer and a reflux condenser were placed 90 g (0.284 mol) of 6-methoxy-7-(3-chloropropoxy)quinazolin-4-one prepared by procedures similar to those of Reference Example V-1, 94 mL (1.13 mol) of hydrochloric acid (12 mol/L, and 180 mL of methanol. The resulting mixture was stirred for one hour at room temperature. After the reaction was complete, 360 mL of acetone was added to the reaction mixture. The resulting mixture was cooled to 5° C. and stirred for one hour. The precipitated crystalline product was filtered to give 113 g of 6-methoxy-7-(3-morpholinopropoxy)quinazolin-4-one hydrochloride as a crude crystalline product (purity: 99.16% in terms of area percentage determined by high performance liquid chromatography). Subsequently, 105 g of the crude crystalline product was mixed with 700 mL of methanol. The mixture was stirred at 60° C. for one hour. After the stirring was complete, the mixture was cooled to room temperature, to precipitate a crystalline product. The crystalline product was collected by filtration and dried under reduced pressure to give 98 g of 6-methoxy-7-(3-morpholinopropoxy)quinazolin-4-one hydrochloride (purity: 99.74% in terms of area percentage determined by high performance liquid chromatography).

Workup

  1. customIn a 1,000 mL volume glass vessel equipped with a stirrer
  2. temperatureThe resulting mixture was cooled to 5° C.
  3. stirringstirred for one hour
  4. filtrationThe precipitated crystalline product was filtered

Sources & evidence

ORD record
ord-5750f43698944adfba3a66ce05a5e6bb
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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