Isobutyraldehyde → 3,4-dihydro-4-isobutyl-7-nitro-2H-1,4-benzoxazine

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Reaction Steps

This compound was prepared by General Method 3 (EXAMPLE 1) from 3,4-dihydro-7-nitro-2H-1,4-benzoxazine (EXAMPLE 1) (550 mg, 3.0 mmol), isobutyraldehyde (1.65 g, 22.8 mmol) and NaBH3CN (959 mg, 15 mmol) to afford 713 mg (99%) of 3,4-dihydro-4-isobutyl-7-nitro-2H-1,4-benzoxazine, an yellow solid. Data for 3,4-dihydro-4-isobutyl-7-nitro-2H-1,4-benzoxazine: Rf 0.75 (3:2 EtOAc:hexanes); 1H NMR (400 MHz, CDCl3) δ 7.78 (dd, 1H, J=9.0, 2.6), 7.66 (d, 1H, J=2.6), 6.55 (d, 1H, J=9.2), 4.21 (t, 2H, J=4.5), 3.52 (t, 2H, J=4.6), 3.16 (d, 2H, J=7.4), 3.12 (hept, 1H, J=6.9), 0.97 (d, 6H, J=6.7).

Provenance & Evidence