Cyanoacetamide → 2-Oxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile

HRID 577791Notes

Reaction equation

HRID 577791 reaction equation
[Na].[CH:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=O)=O.[C:11]([CH2:13][C:14]([NH2:16])=[O:15])#[N:12].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1.ClCCl.C(OCC)(=O)C.C(OCC)C.C(O)(=O)C>[O:15]=[C:14]1[C:13]([C:11]#[N:12])=[CH:2][C:4]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[NH:16]1

Participants

10

Reactant 4

HCID 7898CyanoacetamideHCID 5360545SodiumHCID 9793820Piperidine, acetateHCID 121975852-Oxocyclohexanecarbaldehyde

Product 1

HCID 27682602-Oxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrileYield 318.9%

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium salt of 2-formylcyclohexanone (16.0 g, 10.8 mmol) in toluene (300 mL) was added cyanoacetamide (22.00 g, 0.237 mol), and the reaction was allowed to stir at room temperature for 1 h. After this time, a 2M solution of piperidine acetate in dichloromethane (25 mL) was added, and the reaction was refluxed for 24 h. The reaction mixture was then cooled to 0° C., and acidified with acetic acid. The resulting suspension was filtered and the precipitate was washed with toluene. The filtrate was concentrated to give a sticky residue, which was was treated with diethyl ether followed by ethyl acetate, to provide 2-oxo-1,2,5,6,7,8-hexahydro-quinoline-3-carbonitrile as a fine solid (6.00 g), yield: 31.8%.

Workup

  1. temperaturethe reaction was refluxed for 24 h
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. filtrationThe resulting suspension was filtered
  4. washthe precipitate was washed with toluene
  5. concentrationThe filtrate was concentrated
  6. customto give a sticky residue, which

Sources & evidence

ORD record
ord-cd6a7c9da68f49f7b56c819ff997c94a
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

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