3,4-Dihydro4-(2-dimethylaminoethyl)-6-nitro-2H-1,4-benzoxazine → 6-Amino-3,4-dihydro-4-(2-dimethylaminoethyl)-2H-1,4-benzoxazine

Participants

Reaction Steps

To an oven dried, argon purged 100 mL round bottom flask fitted with a magnetic stirbar was added N,N-dimethyl-2-(6-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethanamine (0.10 g, 0.398 mmol) and EtOH (10 mL). At this time, stirring of the reaction began. 10% Pd—C (0.042 g, 0.040 mmol) was added, the flask was evacuated, and the mixture was subjected to hydrogenation under standard conditions (atmospheric H2 pressure using a balloon). After 3 hours, the mixture was filtered through a pad of Celite and washed with ethanol. The pale peach colored solution, which darkened upon exposure to air, was concentrated to approximately 10 mL to yield the title compound. This compound was utilized immediately in the next step. ESI-MS (m/z, %): 222 (MH+, 100).

Provenance & Evidence