Hydrochloric Acid → 2-(4-Chloro-3-dibutylcarbamoyl-5-methyl-pyrazol-1-yl)-5-methoxy-benzoic acid

HRID 2274579Notes

Reaction equation

HRID 2274579 reaction equation
[CH2:1]([N:5]([CH2:25][CH2:26][CH2:27][CH3:28])[C:6]([C:8]1[C:12]([Cl:13])=[C:11]([CH3:14])[N:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[C:23]#N)[N:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[OH-:29].[K+].Cl.C[OH:33].C(Cl)Cl>C(O)C.O>[Cl:13][C:12]1[C:8]([C:6](=[O:7])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:25][CH2:26][CH2:27][CH3:28])=[N:9][N:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[C:23]([OH:33])=[O:29])[C:11]=1[CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21226129Dichloromethane methanolHCID 896495864-Chloro-1-(2-cyano-4-methoxy-phenyl)-5-methyl-1H-pyrazole-3-carboxylic acid dibutylamide

Product 1

HCID 896470572-(4-Chloro-3-dibutylcarbamoyl-5-methyl-pyrazol-1-yl)-5-methoxy-benzoic acidYield 39%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-Chloro-1-(2-cyano-4-methoxy-phenyl)-5-methyl-1H-pyrazole-3-carboxylic acid dibutylamide (1.3 g, 3.2 mmol) and potassium hydroxide (1.2 g, 21 mmol) in ethanol (5 mL) and water (5 mL) was microwaved at 150° C. for 90 minutes. The pH was adjusted to about 5 with aqueous HCl solution (15 N). The solvent was removed in vacuo. The crude material was eluted through a silica gel column with a 10 to 100% ethyl acetate/heptane and then 1 to 20% methanol/methylene chloride gradient to afford the title compound (0.53 g, 39% yield) as a white solid. MS (ESI) [m/e, (M+H)+]=422.4.

Workup

  1. customwas microwaved at 150° C. for 90 minutes
  2. customThe solvent was removed in vacuo
  3. washThe crude material was eluted through a silica gel column with a 10 to 100% ethyl acetate/heptane

Sources & evidence

ORD record
ord-1a481e62f3b548b99c3d28ad582bd8cd
Source dataset
uspto-grants-2015_09
Patent number
US09126980B2

Reaction notes

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