METHYL 4-OXO-3,4-DIHYDROQUINAZOLINE-8-CARBOXYLATE synthesis
- Product Name:METHYL 4-OXO-3,4-DIHYDROQUINAZOLINE-8-CARBOXYLATE
- CAS Number:1000578-10-8
- Molecular formula:C10H8N2O3
- Molecular Weight:204.18
67-56-1
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Yield:1000578-10-8 94%
Reaction Conditions:
Stage #1:methanol;4-oxo-3,4-dihydro-quinazoline-8-carboxylic acid with sulfuric acid for 48 h;Reflux;
Stage #2: with sodium hydroxide; pH=~ 8 at 20;
Steps:
1
4-oxo-3,4-dihydroquinazoline-8-carboxylic acid (5.0 g, 26.3 mmol) was treated with a solution of sulfuric acid ((1.2 equivalents) in anhydrous MeOH (100 mL) under refluxing for 2 days. After cooling to rt, 2N NaOH solution was added to the reaction mixture to adjust pH~8. After removal of MeOH, methyl ester was collected by filtration, and washing with water and ethyl acetate as pale yellow solid in 94% yield. 1HNMR (in DMSO): 3.84 (s, 3H), 7.42 (t, J=7.6 Hz, 1 H), 7.85 (d, J=6.9 Hz, 1 H), 8.16 (s, 1 H), 8.20 (d, J=7.8 Hz, 1 H). Mass: M+H+: 205. 2.
References:
MERCK PATENT GMBH;SUTTON, Amanda E.;RICHARDSON, Thomas E.;HUCK, Bayard R.;KARRA, Srinivasa R.;CHEN, Xiaoling;XIAO, Yufang;GOUTOPOULOS, Andreas;LAN, Ruoxi;PERREY, David;VANDEVEER, Harold, George;LIU-BUJALSKI, Lesley;STIEBER, Frank;HODOUS, Brian L.;QIU, Hui;JONES, Reinaldo C.;HEASLEY, Brian WO2010/93419, 2010, A1 Location in patent:Page/Page column 173; 194
39622-79-2
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1000578-10-8
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