Malononitrile → Ethyl 4-[2-(5-amino-4-cyanofuran-3-yl)ethyl]benzoate

HRID 1656565Notes

Reaction equation

HRID 1656565 reaction equation
[OH:1][CH2:2][C:3](=O)[CH2:4][CH2:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1.[C:18](#[N:22])[CH2:19][C:20]#[N:21].C(N(CC)CC)C>C(O)C>[NH2:22][C:18]1[O:1][CH:2]=[C:3]([CH2:4][CH2:5][C:6]2[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=2)[C:19]=1[C:20]#[N:21]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8471TriethylamineHCID 10609833Ethyl 4-(4-hydroxy-3-oxobutyl)benzoate

Product 1

HCID 10826899Ethyl 4-[2-(5-amino-4-cyanofuran-3-yl)ethyl]benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.36 g (10 mmol) of ethyl 4-(4-hydroxy-3-oxobutyl)benzoate, 0.66 g. (10 mmol) of malononitrile, and 1.01 g (10 mmol) of triethylamine in 10 mL of ethanol is stirred at 25° C. for 10 hours. Ethyl 4-[2-(2-amino-3-cyanofur-4-yl)ethyl]benzoate is formed as a solid and can be collected by filtration. After washing with a small amount of methylene chloride and drying, a white solid is obtained; m.p. 195°-197° C. Anal. calcd for C16H16N2O3 : C, 67.60; H, 5.67; N, 9.85 Found: C, 67.85; H, 5.71; N, 10.14.

Sources & evidence

ORD record
ord-90eb5be476ce4e93a23abc4897f591f6
Source dataset
uspto-grants-1993_10
Patent number
US05254687

Reaction notes

Loading…