Formamide → 6-Methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one

HRID 1767719Notes

Reaction equation

HRID 1767719 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([NH2:24])=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[C:6]([O:8]CC)=O.[CH:25]([NH2:27])=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:11](=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1)[N:24]=[CH:25][NH:27][C:6]2=[O:8]

Participants

3

Reactant 2

HCID 713FormamideHCID 11809903Ethyl 3-methoxy-4-(3-morpholinopropoxy)-6-aminobenzoate

Product 1

HCID 1354371166-Methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-oneYield 68%

Conditions

Temperature
125 °C

Procedure

A solution of ethyl 3-methoxy-4-(3-morpholinopropoxy)-6-aminobenzoate (130 g, 384 mmol) in formamide (280 ml) was heated at 180° C. for 3 hours, during which time a small amount (25 ml) of liquid distilled out of the reaction. The reaction was cooled to 125° C. and the excess formamide was evaporated in vacuo. Trituration of the solid residue with isopropanol (100 ml), followed by drying in vacuo, yielded 6-methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one (83.0 g, 68% yield) as a pale brown solid:

Workup

  1. distillationdistilled out of the reaction
  2. customthe excess formamide was evaporated in vacuo
  3. customby drying in vacuo

Sources & evidence

ORD record
ord-1dbca152af8040fd8dae71600d434545
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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