Methanol → 6-(3-chloropropoxy)-7-methoxyquinazolin-4(3H)-one

HRID 384817Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:18])[C:6](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][Cl:17])[C:7](OC)=[O:8].C([O-])([O-])OC.C([O-])(=O)C.[NH4+:28].[CH3:29]O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([C:7](=[O:8])[NH:28][CH:29]=[N:18]2)=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][Cl:17]

Participants

Conditions

Temperature: 25 °C

Procedure

In a 10 mL volume stainless pressure-resistant vessel equipped with a stirrer and a thermometer were placed 1.0 g (3.7 mmol) of methyl 4-methoxy-5-(3-chloropropoxy)-anthranilate, 0.93 g (8.8 mmol) of methyl orthoformate, 0.67 g (8.8 mmol) of ammonium acetate, and 5 mL of methanol. The vessel was closed, and the reaction was carried out at 90-95° C. for 8 hours. After the reaction was complete, 50 mL of water was added to the reaction mixture. The aqueous reaction mixture was stirred at 25° C. for one hour, to precipitate a crystalline product. The crystalline product was collected by filtration and dried at 60° C. under reduced pressure, to give 0.89 g (isolated yield: 91%) of 7-methoxy-6-(3-chloropropoxy)quinazolin-4-one as a white crystalline product.

Workup

customIn a 10 mL volume stainless pressure-resistant vessel equipped with a stirrer
customThe vessel was closed
customto precipitate a crystalline product
filtrationThe crystalline product was collected by filtration
customdried at 60° C. under reduced pressure

Sources & evidence

ORD record: ord-15d3142af5c74355b11d24bc8cdcde3c
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367824B2

Reaction notes

Loading…