4-(2-(Dimethylamino)ethyl)-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one → 7-Amino-4-(2-(dimethylamino)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1917131Notes

Reaction equation

HRID 1917131 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:10](=[O:11])[CH2:9][O:8][C:7]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:6]1=2>C(O)C.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:6]2[N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:19])[C:10](=[O:11])[CH2:9][O:8][C:7]=2[CH:12]=1

Participants

4

Reactant 1

HCID 591440824-(2-(Dimethylamino)ethyl)-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one

Product 1

HCID 242533077-Amino-4-(2-(dimethylamino)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(2-(dimethylamino)ethyl)-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (0.5 g, 1.884 mmol) in dry ethanol (5 mL) was treated with Pd—C (˜0.05 g) and purged with hydrogen gas. The flask was evacuated and purged with hydrogen gas (twice) and stirred at room temperature under hydrogen atm. (balloon pressure) for 2 hours. The reaction was filtered through a Celite bed and washed with methanol (3×10 mL). The combined organic layers were evaporated to obtain the crude title compound (0.44 g, quantitative) as a solid. 1H NMR (DMSO-d6) δ 2.16 (s, 6H), 2.36 (t, 2H, J=6.9 Hz), 3.88 (t, 2H, J=6.9 Hz), 4.47 (s, 2H), 5.01 (s, 2H), 6.21 (d, 1H, J=2.1 Hz), 6.25 (dd, 1H, J=2.7, 8.5 Hz), 6.84 (d, 1H, J=8.4 Hz); ESI-MS (m/z, %): 236 (MH+, 31), 191 (100).

Workup

  1. custompurged with hydrogen gas
  2. customThe flask was evacuated
  3. custompurged with hydrogen gas (twice) and
  4. filtrationThe reaction was filtered through a Celite bed
  5. washwashed with methanol (3×10 mL)
  6. customThe combined organic layers were evaporated

Sources & evidence

ORD record
ord-cacace99bd3c4236b23af3971a6f0b4d
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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