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4-Hydroxy-6-methylquinazoline

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4-Hydroxy-6-methylquinazoline manufacturers

4-Hydroxy-6-methylquinazoline Basic information
Product Name:4-Hydroxy-6-methylquinazoline
Synonyms:BUTTPARK 51\07-11;3,4-Dihydro-6-methyl-4-oxoquinazoline;3,4-Dihydro-6-methyl-4-oxoquinazoline 98%;4-Hydroxy-6-methylquinazoline 97%;4-Hydroxy-6-methylquinazoline97%;6-methyl-4-quinazolinone;6-methylquinazolin-4-ol;6-Methylquinazolin-4(3H)-one 98%
CAS:19181-53-4
MF:C9H8N2O
MW:160.17
EINECS:
Product Categories:blocks;Heterocycles;Quinolines
Mol File:19181-53-4.mol
4-Hydroxy-6-methylquinazoline Structure
4-Hydroxy-6-methylquinazoline Chemical Properties
Melting point 238-240
Boiling point 334.6±35.0 °C(Predicted)
density 1.26±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka2.06±0.20(Predicted)
AppearanceWhite to off-white Solid
Safety Information
Hazard Codes Xi
Hazard Note Irritant
HS Code 2933399990
MSDS Information
4-Hydroxy-6-methylquinazoline Usage And Synthesis
Synthesis
2-AMINO-5-METHYLBENZAMIDE

40545-33-3

Trimethoxymethane

149-73-5

4-HYDROXY-6-METHYLQUINAZOLINE

19181-53-4

Concentrated hydrochloric acid (4.16 mL, 49.9 mmol) was slowly added to a mixed solution containing commercially available 2-amino-5-methylbenzamide (5.00 g, 33.3 mmol) and trimethyl orthoformate (51.0 mL, 466 mmol) at 0 °C. The reaction mixture was stirred continuously for 2 hours at room temperature. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue obtained was diluted with distilled water and neutralized with 2 M aqueous sodium hydroxide solution to neutral. Subsequently, the precipitated solid product was collected by filtration and washed sequentially with distilled water, methanol, and ether to finally obtain 6-methyl-4-hydroxyquinazoline (15) as a white powdery solid (4.33 g, 81% yield). The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6): δ 2.44 (3H, s), 7.57 (1H, d, J = 8.4 Hz), 7.62-7.66 (1H, m), 7.91-7.93 (1H, m), 8.03 (1H, s), 12.2 (1H, bs).

References[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 19, p. 5487 - 5505
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 545 - 548
[3] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 383 - 391
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