Ammonium Acetate → 6,7-Bis(2-methoxyethoxy)quinazolin-4(1H)-one

HRID 384764Notes

Reaction equation

HRID 384764 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH2:22])[C:9](=[CH:15][C:16]=1[O:17][CH2:18][CH2:19][O:20][CH3:21])[C:10](OCC)=[O:11].[CH:23]([O-])([O-])OC.C([O-])(=O)C.[NH4+:32]>CO>[CH3:21][O:20][CH2:19][CH2:18][O:17][C:16]1[CH:15]=[C:9]2[C:8](=[CH:7][C:6]=1[O:5][CH2:4][CH2:3][O:2][CH3:1])[N:22]=[CH:23][NH:32][C:10]2=[O:11]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 11347513Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoateHCID 53629101Methylorthoformate

Product 1

HCID 1354093056,7-Bis(2-methoxyethoxy)quinazolin-4(1H)-oneYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 10-mL volume stainless steel pressure-resistant vessel were placed 1.02 g (3.3 mmol) of ethyl 4,5-bis(2-methoxyethoxy)anthranilate, 0.96 g (9.1 mmol) of methyl orthoformate, 0.69 g (9.1 mmol) of ammonium acetate, and 5.0 mL of methanol. The reaction was carried out at 110° C. for 6 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 20 mL of methanol. The crystalline product was collected by filtration and dried under reduced pressure to give 0.87 g (isolated yield: 91%) of 6,7-bis(2-methoxyethoxy)quinazolin-4-one as a white crystalline product.

Workup

  1. customIn a 10-mL volume stainless steel pressure-resistant vessel were placed
  2. concentrationconcentrated under reduced pressure
  3. customThen, the concentrate was recrystallized from 20 mL of methanol
  4. filtrationThe crystalline product was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-0c5cd95fdacf4a3e8b90e0999b61a30d
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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