Potassium Carbonate → [3,5-dimethyl-1-(2-chloro-4-nitrobenzyl)-1H-pyrazol-4-yl]acetic acid ethyl ester

HRID 409388

Reaktionsgleichung

Reaktionsgleichung von HRID 409388
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[C:7]([CH3:12])=[N:8][NH:9][C:10]=1[CH3:11])[CH3:2].[Cl:14][C:15]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:16]=1[CH2:17]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C.CO>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[C:7]([CH3:12])=[N:8][N:9]([CH2:17][C:16]2[CH:19]=[CH:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][C:15]=2[Cl:14])[C:10]=1[CH3:11])[CH3:2]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 30163681-(Bromomethyl)-2-chloro-4-nitrobenzeneHCID 16394806ethyl 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetate

Produkt 1

HCID 66707495[3,5-dimethyl-1-(2-chloro-4-nitrobenzyl)-1H-pyrazol-4-yl]acetic acid ethyl esterAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of (3,5-dimethyl-1H-pyrazol-4-yl)acetic acid ethyl ester (1.40 g, 7.7 mmol) and 2-chloro-4-nitrobenzyl bromide (4.60 g, 20.7 mmol) in 20 mL acetonitrile is added K2CO3 (1.59 g, 11.5 mmol) and the mixture is stirred for 48 hours at room temperature. The solvent is removed by evaporation and the residue is dissolved in dichloromethane/water. After extraction with dichloromethane the organic layer is dried over Na2SO4 and evaporated under reduced pressure to yield 2.79 g of [3,5-dimethyl-1-(2-chloro-4-nitro-benzyl)-1H-pyrazol-4-yl]-acetic acid ethyl ester (ESI mass spectrum: [M+H]+=352; Retention time: 1.95 min (method A). b) To a solution [3,5-dimethyl-1-(2-chloro-4-nitrobenzyl)-1H-pyrazol-4-yl]acetic acid ethyl ester (2.39 g, 6.8 mmol) in methanol (40 mL) is added Raney nickel (250 mg) and the mixture is hydrogenated. The catalyst is filtered off and the filtrate is concentrated under reduced pressure to yield 1.18 g of the title compound (ESI mass spectrum: [M+H]+=322; Retention time HPLC: 1.76 min (method A)).

Aufarbeitung

  1. customThe solvent is removed by evaporation
  2. dissolutionthe residue is dissolved in dichloromethane/water
  3. extractionAfter extraction with dichloromethane the organic layer
  4. dry with materialis dried over Na2SO4
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d1e5ffa5fb3c48e6aed14311351fa7d4
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759386B2

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