Methanol → HCID 135589776, compound

HRID 384818Notes

Reaction equation

HRID 384818 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][CH2:18][Cl:19].C([O-])([O-])OC.C([O-])(=O)C.[NH4+:29].[CH3:30]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][CH2:18][Cl:19])[N:13]=[CH:30][NH:29][C:8]2=[O:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 517165Ammonium AcetateHCID 10286203HCID 10286203, compoundHCID 53629101Methylorthoformate

Product 1

HCID 135589776HCID 135589776, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

In a 10 mL volume stainless pressure-resistant vessel equipped with a stirrer and a thermometer were placed 1.1 g (3.5 mmol) of methyl 5-methoxy-4-(4-chlorobutoxy)-anthranilate, 0.92 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 0.94 g (isolated yield: 96%) of 6-methoxy-7-(4-chlorobutoxy)quinazolin-4-one as a gray crystalline product.

Workup

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

Sources & evidence

ORD record
ord-d73df4b868e84452a857d9ecf90ea218
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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