8-Azido-5,6,7,8-tetrahydroquinoline → 8-Amino-5,6,7,8-tetrahydroquinoline

HRID 353356Notes

Reaction equation

HRID 353356 reaction equation
[N:1]([CH:4]1[C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:7][CH2:6][CH2:5]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH:4]1[C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 227087698-Azido-5,6,7,8-tetrahydroquinoline

Product 1

HCID 113555648-Amino-5,6,7,8-tetrahydroquinolineYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the azide (41.0 g, 0.256 mol) in methanol (250 mL) was added Pd/C (10%, 4.1 g) and the mixture was hydrogenated at 30 psi on a Parr shaker. The mixture was filtered through celite and the cake was washed with methanol. The combined filtrates were evaporated and the residual oil was distilled (Kugelrohr, bp 115-140° C. @ 0.2 Torr) to provide 26.8 g (71%) of 8-amino-5,6,7,8-tetrahydroquinoline (AMD7488) as a pale yellow oil. 1H NMR (MeOH-d4) δ 1.81-1.98 (m, 2H), 2.03-2.15 (m, 1H), 2.38-2.46 (m, 1H), 2.88-2.92 (m, 2H), 4.41 (dd, 1H, J=9.3, 6.3 Hz), 7.30 (dd, 1H, J=7.5, 4.5 Hz), 7.62 (d, 1H, J=7.5 Hz), 8.47 (d, 1H, J=4.5 Hz); 13C NMR (MeOH-d4) δ 21.12, 28.72, 28.89, 52.28, 124.86, 134.35, 138.96, 148.49, 152.57. ES-MS m/z 149 (M+H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe cake was washed with methanol
  3. customThe combined filtrates were evaporated
  4. distillationthe residual oil was distilled (Kugelrohr, bp 115-140° C. @ 0.2 Torr)

Sources & evidence

ORD record
ord-38bfd53c89bc4b6c9c18981a94d67363
Source dataset
uspto-grants-2004_06
Patent number
US06750348B1

Reaction notes

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