Ethyl 2-(methoxyimino)-4-oxopentanoate → Ethyl 1-(3-cyano-4-methylphenyl)-3-methyl-5-pyrazole-carboxylate

HRID 376430Notes

Reaction equation

HRID 376430 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:10][NH2:11])[CH:6]=[CH:7][C:8]=1[CH3:9])#[N:2].CON=[C:15]([CH2:21][C:22](=O)[CH3:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([N:10]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:21][C:22]([CH3:23])=[N:11]2)[CH:6]=[CH:7][C:8]=1[CH3:9])#[N:2]

Participants

4

Reactant 2

HCID 589173Ethyl 2-(methoxyimino)-4-oxopentanoateHCID 185492753-Cyano-4-methylphenyl-hydrazine

Product 1

HCID 18549349Ethyl 1-(3-cyano-4-methylphenyl)-3-methyl-5-pyrazole-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Part A: Ethyl 1-(3-cyano-4-methylphenyl)-3-methyl-5-pyrazole-carboxylate was prepared as colorless crystals following the standard condensation (3-cyano-4-methylphenyl-hydrazine and ethyl 2-(N-(methoxy)imino)-4-oxopentanoate in acetic acid) reaction protocol discussed previously. 1HNMR (CDCl3) δ: 7.68 (s, 1H), 7.57 (dd, 1H), 7.58 (d, 1H), 6.82 (s, 1H), 4.24 (q, 2H), 2.40 (s, 3H0, 2.37 (s, 3H), 1.27 (t, 3H) ppm; ESI mass spectrum analysis (270 (M+H, 100).

Sources & evidence

ORD record
ord-9354060d02ed43f49e13db9523f6b8c5
Source dataset
uspto-grants-2000_02
Patent number
US06020357

Reaction notes

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