Hydrochloric Acid → Methyl 4-hydroxyquinazoline-6-carboxylate

HRID 1616108Notes

Reaction equation

[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][NH:3]1.Cl.O1CCOC[CH2:17]1>CO>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:17])=[O:13])[CH:10]=2)[N:5]=[CH:4][NH:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a sealed tube was added 4-oxo-3,4-dihydroquinazoline-6-carboxylic acid (0.88 g, 4.6 mmol), methanol (70 mL) and 4.0 M hydrochloric acid in 1,4-dioxane (4.63 mL, 18.5 mmol). The reaction mixture was heated to 90° C. and stirred overnight. The mixture was then cooled to rt, and concentrated to yield methyl 4-oxo-3,4-dihydroquinazoline-6-carboxylate (0.94 g, quant). LC-MS: (FA) ES+ 205; 1H NMR (400 MHz, DMSO) δ 8.65 (d, J=2.1 Hz, 1H), 8.30 (dd, J=8.5, 2.1 Hz, 1H), 8.22 (s, 1H), 7.77 (d, J=8.5 Hz, 1H), 3.88 (s, 3H).

Workup

temperatureThe mixture was then cooled to rt
concentrationconcentrated

Sources & evidence

ORD record: ord-8d26500356434adbbe6614fe318783e5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765773B2

Reaction notes

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