Phenelzine → Ethyl 5-methyl-1-phenethylpyrazole-3-carboxylate

HRID 1825333Notes

Reaction equation

[CH2:1]([NH:9][NH2:10])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O=[C:12]([CH2:18][C:19](=O)[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>>[CH3:20][C:19]1[N:9]([CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:10]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:18]=1

Participants

Reactant 2

HCID 3675Phenelzine

HCID 69208Ethyl 2,4-dioxovalerate

Product 1

HCID 22145419Ethyl 5-methyl-1-phenethylpyrazole-3-carboxylate

Procedure

The title compound was prepared from phenethyl hydrazine (3.92 g, 0.029M) (obtained by the method of J. H. Biel U.S. Pat. No. 3,000,903) and ethyl 2,4-dioxovalerate (4.55 g, 0.029M) as described in Example 1, Preparation 1 as a yellow oil (3.84 g, 52%); νmax(CH2Cl2) 1720 cm−1; δH(CDCl3) 1.40 (3H, t, J7 Hz), 1.90 (3H, s), 3.14 (2H, t, J7 Hz), 4.30 (2H, t, J7 Hz), 4.41 (2H, q, J7 Hz), 6.48 (1H, s), 6.97-7.09 (2H, m), and 7.20-7.37 (3H, m); E.I. m/e 258.

Workup

customobtained by the method of J

Sources & evidence

ORD record: ord-3c1b63d8362548ebb66366d49bfb4d1b
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045619B2

Reaction notes

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