3,4-Dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester Chemical Properties

Melting point:

73-74 °C

Boiling point:

337.7±41.0 °C(Predicted)

Density 

1.198±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

3.60±0.20(Predicted)

Appearance

White to light brown Solid

Safety Information

HS Code 

2934999090

3,4-Dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester Usage And Synthesis

Synthesis

Step 2. Methyl 3-amino-4-hydroxybenzoate (4.2 g, 25.4 mmol) was dissolved in dimethylformamide (85 mL) and K2CO3 (14.2 g, 102.9 mmol, 4 eq.) and 1,2-dibromoethane (19.3 g, 102.9 mmol, 4 eq.) were added sequentially. The reaction mixture was stirred at 70 °C overnight. Upon completion of the reaction, the insoluble solids were removed by filtration. The filtrate was concentrated under reduced pressure to remove the solvent and the residue was purified by fast column chromatography (eluent: heptane/ethyl acetate gradient) to afford methyl 3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylate (3.65 g, light yellow solid). The product was identified by mass spectrometry (ISP): m/e = 235.1 (M + CH3CN+); NMR hydrogen spectrum (300 MHz, CDCl3) δH: 7.36 (1H, dd, J = 8.5, 2.0), 7.30 (1H, d, J = 2.0), 6.78 (1H, d, J = 8.5), 4.30 (2H, m), 3.85 (3H , s), 3.43 (2H, m).

References

[1] Patent: US2007/191603, 2007, A1. Location in patent: Page/Page column 25
[2] Patent: US2009/176775, 2009, A1. Location in patent: Page/Page column 30
[3] Patent: EP2172453, 2010, A1. Location in patent: Page/Page column 15-16

3,4-Dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester(758684-29-6)Related Product Information

• 3,4-Dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester
• METHYL 2-CYANO-3,4-DIHYDRO-2H-BENZO[B][1,4]OXAZINE-6-CARBOXYLATE
• METHYL 3,4-DIHYDRO-3-OXO-2H-BENZO[B][1,4]OXAZINE-6-CARBOXYLATE
• ETHYL 3-OXO-3,4-DIHYDRO-2H-BENZO[B][1,4]OXAZINE-6-CARBOXYLATE
• 3,4-DIHYDRO-2H-BENZO[1,4]OXAZINE-6-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE
• methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate