Water → 1-(3-Carboxybenzyl)quinazoline-2,4(1H,3H)-dione

HRID 927292Notes

Reaction equation

HRID 927292 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:21]=[CH:22][CH:23]=1)[CH2:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[NH:11][C:10]1=[O:20])=[O:4].[OH-].[Na+].O>CO>[C:3]([C:5]1[CH:6]=[C:7]([CH:21]=[CH:22][CH:23]=1)[CH2:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[NH:11][C:10]1=[O:20])([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68388893HCID 68388893, compound

Product 1

HCID 683887821-(3-Carboxybenzyl)quinazoline-2,4(1H,3H)-dioneYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(3-methoxycarbonylbenzyl)quinazoline-2,4(1H,3H)-dione (1.6 g, 5.2 mmol), NaOH (0.31 g, 7.7 mmol), water (40 mL) and methanol (40 mL) were added into a 250 mL three-mouth flask. The mixture was refluxed and reacted for 3 hours. The methanol was removed via evaporation under reduced pressure after the reaction was finished. The mixture was adjusted to pH=2-3 by 3N HCl, forming many precipitates. The mixture was filtered and the solid was washed by water and methonal. The solids were dried to give the title compound as white solid (1.2 g, 78% yield). 1H NMR (300 M, DMSO-d6): 13.09 (brs, 1H), 11.77 (s, 1H), 8.01 (dd, J=7.7 and 1.4 Hz, 1H), 7.84-7.80 (m, 2H), 7.66-7.61 (m, 1H), 7.53 (d, J=7.8 Hz, 1H), 7.44 (t, J=7.7 Hz, 1H), 7.27-7.21 (m, 2H), 5.36 (s, 2H). MS: m/z 297.1 [M+H]+.

Workup

  1. temperatureThe mixture was refluxed
  2. customreacted for 3 hours
  3. customThe methanol was removed via evaporation under reduced pressure after the reaction
  4. customforming many precipitates
  5. filtrationThe mixture was filtered
  6. washthe solid was washed by water
  7. customThe solids were dried

Sources & evidence

ORD record
ord-b5c8d0382a1e48858b625b1618edacff
Source dataset
uspto-grants-2016_03
Patent number
US09290460B2

Reaction notes

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