Triethylamine → Ethyl 3-phenyl-3-(pyridazin-4-yl)propanoate

HRID 512195Notes

Reaction equation

HRID 512195 reaction equation
[C:1]1(/[C:7](/[C:14]2[CH:19]=[CH:18][N:17]=[N:16][CH:15]=2)=[CH:8]\[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(NN)(C1C=CC(C)=CC=1)(=O)=O.CCN(CC)CC>C1(C)C=CC=CC=1>[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][N:17]=[N:16][CH:15]=2)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15303P-ToluenesulfonylhydrazideHCID 86716221(E)-Ethyl 3-phenyl-3-(pyridazin-4-yl)acrylate

Product 1

HCID 86716222Ethyl 3-phenyl-3-(pyridazin-4-yl)propanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (E)-ethyl 3-phenyl-3-(pyridazin-4-yl)acrylate (1.8 g, 7.09 mmol) in PhMe (40 mL), TsNHNH2 (2.64 g, 14.2 mmol) and Et3N (2.15 g, 21.3 mmol) was added, the resulting mixture was heated to 100° C. overnight. The reaction was detected by TLC, TLC showed the appearance of desired product, then, the solvent was removed under reduced pressure, H2O was added and extracted with AcOEt (3×50 ml), the combined organic layers were washed by brine, dried over Na2SO4 and concentrated to get the crude product, which was purified by column chromatography on silica gel (Petroleum Ether: EtOAc=3:2) to afford ethyl 3-phenyl-3-(pyridazin-4-yl)propanoate (1.20 g, yield: 66%). 1H NMR (CDCl3 400 MHz):δ9.12 (d, J=2.0 Hz, 1H), 9.09 (d, J=6.8 Hz, 1H), 7.40-7.24 (m, 4H), 7.20 (d, J=7.2 Hz, 2H), 4.56 (t, J=8.0 Hz, 1H), 4.08 (q, J=7.2 Hz, 2H), 3.09 (d, J=8.0 Hz, 2H), 1.15 (t, J=7.2 Hz, 3H).

Sources & evidence

ORD record
ord-d8c0a6a1c8694d0d979faeb0e2bec1ce
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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