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

HRID 384763Notes

Reaction equation

HRID 384763 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH2:20])[C:9](=[CH:13][C:14]=1[O:15][CH2:16][CH2:17][O:18][CH3:19])[C:10](O)=[O:11].[CH:21]([O-])([O-])OC.C([O-])(=O)C.[NH4+:30]>CO>[CH3:19][O:18][CH2:17][CH2:16][O:15][C:14]1[CH:13]=[C:9]2[C:8](=[CH:7][C:6]=1[O:5][CH2:4][CH2:3][O:2][CH3:1])[N:20]=[CH:21][NH:30][C:10]2=[O:11]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 230330092-Amino-4,5-bis(2-methoxyethoxy)benzoic acidHCID 53629101Methylorthoformate

Product 1

HCID 1354093056,7-Bis(2-methoxyethoxy)quinazolin-4(1H)-oneYield 103.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 10-mL volume stainless steel pressure-resistant vessel were placed 1.00 g (2.8 mmol) of 4,5-bis(2-methoxyethoxy)anthranilic acid, 0.93 g (8.8 mmol) of methyl orthoformate, 0.67 g (8.8 mmol) of ammonium acetate, and 5.0 mL of methanol. The reaction was carried out at 95° C. for 8 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 0.85 g (isolated yield: 83%) 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-79064fdb8a874f8f926860e49a31b8e8
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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