Ammonium Acetate → 6-Methoxy-7-(3-piperidinopropoxy)-3,4-dihydroquinazolin-4-one

HRID 384766Notes

Reaction equation

HRID 384766 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][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[CH:24]([O-])([O-])OC.C([O-])(=O)C.[NH4+:33]>CO>[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][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[N:13]=[CH:24][NH:33][C:8]2=[O:9]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 23033018Methyl 5-methoxy-4-(3-piperidinopropoxy)anthranilateHCID 53629101Methylorthoformate

Product 1

HCID 1354715536-Methoxy-7-(3-piperidinopropoxy)-3,4-dihydroquinazolin-4-oneYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 10-mL volume stainless steel pressure-resistant vessel were placed 1.00 mg (3.1 mmol) of methyl 5-methoxy-4-(3-piperidinopropoxy)anthranilate, 0.99 g (9.3 mmol) of methyl orthoformate, 0.72 g (9.3 mmol) of ammonium acetate, and 5.0 mL of methanol. The reaction was carried out at 120° C. for 5 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and analyzed (according to absolute quantitative analysis) by high performance liquid chromatography. There was produced 0.89 mg (reaction yield: 90%) of 6-methoxy-7-(3-piperidinopropoxy)quinazolin-4-one.

Workup

  1. customIn a 10-mL volume stainless steel pressure-resistant vessel were placed

Sources & evidence

ORD record
ord-573d7672f5e543f2953f6b4fc0ca8618
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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