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

HRID 899667Notes

Reaction equation

HRID 899667 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-a6707fd1b8f94633bdfbce784ea4e442
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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