Ammonium Acetate → 6-Methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

HRID 384765Notes

Reaction equation

HRID 384765 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:7]([C:8](OC)=[O:9])[C:6]([NH2:13])=[CH:5][C:4]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.[CH:24]([O-])([O-])OC.C([O-])(=O)C.[NH4+:33]>CO>[CH3:1][O:2][C:3]1[CH:12]=[C:7]2[C:6](=[CH:5][C:4]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[N:13]=[CH:24][NH:33][C:8]2=[O:9]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 23033010HCID 23033010, compoundHCID 53629101Methylorthoformate

Product 1

HCID 1354371166-Methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-oneYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 100-mL volume stainless steel pressure-resistant vessel were placed 5.80 g (17.9 mmol) of methyl 5-methoxy-4-(3-morpholinopropoxy)anthranilate, 3.79 g (35.8 mmol) of methyl orthoformate, 2.56 g (33.2 mmol) of ammonium acetate, and 30 mL of methanol. The reaction was carried out at 115° C. for 5 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and concentrated under reduced pressure. Then, the concentrate was recrystallized from 100 mL of methanol. The crystalline product was collected by filtration and dried under reduced pressure to give 4.97 g (isolated yield: 87%) of 6-methoxy-7-(3-morpholinopropoxy)-quinazolin-4-one as a white crystalline product.

Workup

  1. customIn a 100-mL volume stainless steel pressure-resistant vessel were placed
  2. concentrationconcentrated under reduced pressure
  3. customThen, the concentrate was recrystallized from 100 mL of methanol
  4. filtrationThe crystalline product was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-731a1a1c3e8248e6b2fb28e169ebe23c
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

Loading…