5-Azido-5,6,7,8-tetrahydroquinoxaline → 5,6,7,8-Tetrahydroquinoxalin-5-amine

HRID 899813Notes

Reaction equation

HRID 899813 reaction equation
[N:1]([CH:4]1[CH2:13][CH2:12][CH2:11][C:10]2[N:9]=[CH:8][CH:7]=[N:6][C:5]1=2)=[N+]=[N-]>[Pd]>[N:9]1[C:10]2[CH2:11][CH2:12][CH2:13][CH:4]([NH2:1])[C:5]=2[N:6]=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 581494935-Azido-5,6,7,8-tetrahydroquinoxaline

Product 1

HCID 120990635,6,7,8-Tetrahydroquinoxalin-5-amineYield 99.9%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A Parr shaker flask was charged with 5-azido-5,6,7,8-tetrahydroquinoxaline (1.81 g, 10.33 mmol) and 10% palladium on carbon (10 wt % of Pd/C; 0.18 g). The reaction vessel was evacuated and filled with nitrogen. Methanol (30 mL) was added and the reaction was hydrogenated at 30 psi for 40 minutes. The reaction mixture was flushed with nitrogen and filtered through a plug of Celite® to provide 5,6,7,8-tetrahydroquinoxalin-5-ylamine as an orange liquid (1.54 g, 99%), which would rapidly turn dark brown. It was stored under an argon atmosphere at −20° C. 1H NMR (CDCl3): δ 1.62-1.79 (m, 1H), 1.80-2.18 (m, 4H), 2.18-2.30 (m, 1H), 2.91-3.01 (m, 2H), 4.07 (dd, 1H, J=8.4, 5.4 Hz), 8.32-8.38 (m, 2H); 13C NMR (CDCl3): δ 19.7, 31.7, 32.2, 51.5, 142.0, 142.5, 152.6, 155.4; MS m/z: 150 (M+H+), 133.

Workup

  1. customThe reaction vessel was evacuated
  2. additionfilled with nitrogen
  3. additionMethanol (30 mL) was added
  4. customThe reaction mixture was flushed with nitrogen
  5. filtrationfiltered through a plug of Celite®

Sources & evidence

ORD record
ord-4e006c79c9d8436d8a92fa7b1a9db2f4
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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