HCID 43082674, compound → 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehyde

Temperature

80 °C

To a 100 mL round-bottomed flask was added methyl 2-(4-formyl-2-nitrophenoxy)acetate (1) (1.381 g, 5.77 mmol) and iron (1.612 g, 28.9 mmol) in AcOH (23 mL). The reaction was stirred at 80° C. for 1 hr. The reaction was concentrated in vacuo and taken up in DCM/MeOH (1:1, 100 mL), filtered and the filtrate was concentrated in vacuo to give 4.3 g crude of a brown solid. The solid was taken up in water and filtered; the solid was washed with water and dried in vacuo to give a light brown solid (0.712 g, 70% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.72 (s, 2 H) 7.14 (d, J=8.34 Hz, 1H) 7.38 (d, J=1.77 Hz, 1H) 7.54 (dd, J=8.21, 1.89 Hz, 1H) 9.84 (s, 1 H) 10.99 (s, 1H). ESI-MS: m/z 178.1 (M+H)+.

1. concentrationThe reaction was concentrated in vacuo
2. filtrationfiltered
3. concentrationthe filtrate was concentrated in vacuo
4. customto give 4.3 g crude of a brown solid
5. filtrationfiltered
6. washthe solid was washed with water
7. customdried in vacuo

ORD record

ord-f0629f86ee1742e08db2e81089ce6d16

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08669249B2