Acetaldehyde → HCID 18416126, compound

Participants

Reaction Steps

This compound was prepared by General Method 3 (EXAMPLE 1) from (±)-3,4-dihydro-3-methyl-7-nitro-2H-1,4-benzoxazine (200 mg, 1.0 mmol), acetaldehyde (455 mg, 10.3 mmol) and NaBH3CN (314 mg, 5.0 mmol) to afford 144 mg (63%) of 4-ethyl-3,4-dihydro-3-methyl-7-nitro-2H-1,4-benzoxazine. Data for (±)-4-ethyl-3,4-dihydro-3-methyl-7-nitro-2H-1,4-benzoxazine: Rf 0.80 (3:2 EtOAc:hexanes); 1H NMR (500 MHz, CDCl3) δ 7.80 (dd, 1H, J=8.9, 2.6), 7.66 (d, 1H, J=2.6), 6.55 (d, 1H, J=9.2), 4.07 (dd, 1H, J=10.7,2.5), 3.96 (dd, 1H, J=10.7, 2.6), 3.60 (m, 1H), 3.55-3.35 (m, 2H), 1.29 (d, 3H, J=6.6), 1.24 (t, 3H, J=7.0).

Provenance & Evidence