Ethyl 6-nitroquinoxaline-2-carboxylate → Ethyl 6-aminoquinoxaline-2-carboxylate

HRID 2273618Notes

Reaction equation

HRID 2273618 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=[N:7]2)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=[N:7]2

Participants

4

Reactant 1

HCID 53485586Ethyl 6-nitroquinoxaline-2-carboxylate

Product 1

HCID 53485587Ethyl 6-aminoquinoxaline-2-carboxylateYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a flask containing compound 7 (2.93 g, 11.9 mmol) in ethanol (500 mL) was added 10% Pd/C (300 mg). The mixture was degassed and stirred under a H2 atmosphere for 3 h 45. The catalyst was removed by filtration through Celite® 545, washed with ethanol (50 mL) and the filtrate was evaporated. The resulting crude product was purified by chromatography (Al2O3, CH2Cl2/EtOH, 99/1, v/v) to afford the title product 8 (1.69 g, 7.79 mmol) as a dark yellow solid. Yield 66%; Rf (Al2O3, CH2Cl2/EtOH, 99/1, v/v) 0.55; mp 181-183° C.; IR (KBr)□ ν 1299, 1487, 1613, 1701, 3202, 3431 □cm−1; 1H NMR (200 MHz, CDCl3) δ 1.49 (t, 3H, J=7 Hz), 4.38 (m, 2H), 4.56 (q, 2H, J=7 Hz), 7.16 (d, 1H, J=2.5 Hz), 7.26 (dd, 1H, J=2.5, 9 Hz), 8.05 (d, 1H, J=9 Hz), 9.35 (s, 1H); MS m/z 217 (M+, 23), 145 (100), 117 (19), 90 (16), 63 (14).

Workup

  1. customThe mixture was degassed
  2. customThe catalyst was removed by filtration through Celite® 545
  3. washwashed with ethanol (50 mL)
  4. customthe filtrate was evaporated
  5. customThe resulting crude product was purified by chromatography (Al2O3, CH2Cl2/EtOH, 99/1

Sources & evidence

ORD record
ord-b604219712d94d01af249a4eb49c18c6
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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