Malononitrile → Ethyl 2-amino-3-cyano-4,7-dihydrofuro[2,3-c]pyridine-6(5H)-carboxylate

HRID 38532Notes

Reaction equation

HRID 38532 reaction equation
[OH:1][CH:2]1[C:7](=O)[CH2:6][CH2:5][N:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3]1.[C:14](#[N:18])[CH2:15][C:16]#[N:17].C(NCC)C>C(O)C>[NH2:18][C:14]1[O:1][C:2]2[CH2:3][N:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:6][C:7]=2[C:15]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8021DiethylamineHCID 58116852Ethyl 3-hydroxy-4-oxopiperidine-1-carboxylate

Product 1

HCID 58116828Ethyl 2-amino-3-cyano-4,7-dihydrofuro[2,3-c]pyridine-6(5H)-carboxylateYield 39.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-hydroxy-4-oxopiperidine-1-carboxylate from Example 35A (4.00 g, 21.4 mmol) was dissolved in ethanol (10 mL), and propanedinitrile (1.41 g, 21.4 mmol) was added. Within 10 min, diethylamine (1.56 g, 21.4 mmol) was added dropwise, whilst the temperature was kept below 35° C. Subsequently, the reaction mixture was stirred for 20 h at rt. The precipitate was collected by suction filtration and washed with ethanol and diethyl ether to yield 2.00 g (39%) of the title compound.

Workup

  1. customwas kept below 35° C
  2. filtrationThe precipitate was collected by suction filtration
  3. washwashed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-1928fa53cf84457eb9827dd4c1a68684
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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