3-(2-[1,3]dioxolan-2-yl-ethyl)-1H-quinazoline-2,4-dione → 3-[2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]propionaldehyde

HRID 1266980Notes

Reaction equation

HRID 1266980 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][CH2:7][N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:19]>CC(C)=O>[O:19]=[C:9]1[N:8]([CH2:7][CH2:6][CH:2]=[O:1])[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10]1

Participants

3

Reactant 1

HCID 185451993-(2-[1,3]dioxolan-2-yl-ethyl)-1H-quinazoline-2,4-dione

Product 1

HCID 185451873-[2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]propionaldehydeYield 95.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-(2-[1,3]dioxolan-2-yl-ethyl)-1H-quinazoline-2,4-dione (0.11 g, 0.43 mmol) 10% sulfuric acid (10 mL) and Acetone (10 mL) was stirred at ambient temperature for 24 hours. Concentration yielded 3-[2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]propionaldehyde (0.09 g, 95%) as an off-white solid. 1H NMR CDCl3 δ9.85 (s, 1H), 8.10-8.06 (m,1H), 7.63-7.57 (m, 1H), 7.24-7.19 (m, 1H), 7.13-7.07 (m, 1H), 4.44-4.40 (m, 2H), 2.85 (dt, 2H, J1,2=2 Hz, J1,3=7 Hz).

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-d21a587fcc4e4855b06e230a1cdc7b7e
Source dataset
uspto-grants-2003_04
Patent number
US06552015B2

Reaction notes

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