Methanol → 6-Methoxy-7-(3-chloropropoxy)quinazolin-4-one

HRID 384816Notes

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][Cl:18].C([O-])([O-])OC.C([O-])(=O)C.[NH4+:28].[CH3:29]O>O>[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][Cl:18])[N:13]=[CH:29][NH:28][C:8]2=[O:9]

Participants

Conditions

Temperature: 5 °C

Procedure

In a 1,000 mL volume stainless pressure-resistant vessel equipped with a stirrer, a thermometer and a pressure gauge were placed 161.5 g (0.59 mol) of methyl 5-methoxy-4-(3-chloropropoxy)anthranilate, 156.5 g (1.48 mol) of methyl orthoformate, 113.7 g (1.48 mol) of ammonium acetate, and 300 mL of methanol. The vessel was closed, and the reaction was carried out at 90-95° C. for 8 hours. The pressure in the vessel was 0.1-0.3 MPa (gauge pressure). After the reaction was complete, 600 mL of water was added to the reaction mixture. The aqueous reaction mixture was stirred at 0-10° C. for one hour, to precipitate a crystalline product. The crystalline product was collected by filtration, washed with 600 mL of water, and dried at 60° C. under reduced pressure, to give 152.8 g (isolated yield: 94%) of 6-methoxy-7-(3-chloropropoxy)quinazolin-4-one as a white crystalline product.

Workup

customIn a 1,000 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
washwashed with 600 mL of water
customdried at 60° C. under reduced pressure

Sources & evidence

ORD record: ord-8ae130703e064775b58066be6087b7cf
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367824B2

Reaction notes

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