Ethyl 8-Azido-4-Oxo-4H-Quinolizine-3-Carboxylate → Ethyl 8-Amino-4-Oxo-4H-Quinolizine-3-Carboxylate

HRID 48911Notes

Reaction equation

HRID 48911 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][N:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8]2=[O:19])=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][N:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8]2=[O:19]

Participants

4

Reactant 1

HCID 20634157Ethyl 8-Azido-4-Oxo-4H-Quinolizine-3-Carboxylate

Product 1

HCID 20634156Ethyl 8-Amino-4-Oxo-4H-Quinolizine-3-CarboxylateYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of ethyl 8-azido-4-oxo-4H-quinolizine-3-carboxylate (14) (253 mg, 1.0 mmol) and 20 mg 5% Pd on carbon in 15 ml ethanol was stirred under ambient hydrogen pressure. The color of the reaction mixture rapidly changed from deep red to dark yellow. After 30 ml of hydrogen was absorbed by the reaction mixture, the catalyst was filtered off and the solvent was evaporated to give ethyl 8-amino-4-oxo-4H-quinolizine-3-carboxylate (15) (221 mg, 94%) as a yellow green powder. M.p.>250° C. 1H NMR (δ, DMSO-d6): 1.23 (t, J=7 Hz, 3H), 4.13 (q, J=7 Hz, 2H), 6.23 (d, J=7 Hz, 1H), 6.53 (d, J=2 Hz, 1H), 6.79 (dd, J=2 Hz, J=7 Hz, 1H), 7.32 (s, 2H), 7.81 (d, J=8 Hz, 1H), 8.94 (d, J=7 Hz, 1H). MS: m/s 232.0837; required for C12H12NO3: 232.0848.

Workup

  1. customAfter 30 ml of hydrogen was absorbed by the reaction mixture
  2. filtrationthe catalyst was filtered off
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c5d6befd5f494032bad53cacbf930c5b
Source dataset
uspto-grants-2004_03
Patent number
US06706528B2

Reaction notes

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