Water → HCID 71116251, compound

HRID 2276883Notes

Reaction equation

HRID 2276883 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([N:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=2)=[C:12]([CH3:23])[C:11]([C:24]([O:26]CC)=[O:25])=[N:10]1.[OH-].[Li+].O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[CH:15]=[CH:16][C:17]([N:20]([CH3:22])[CH3:21])=[CH:18][CH:19]=2)=[C:12]([CH3:23])[C:11]([C:24]([OH:26])=[O:25])=[N:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 71116118HCID 71116118, compound

Product 1

HCID 71116251HCID 71116251, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-(2,4-dichlorophenyl)-5-[4-(dimethylamino)phenyl]-4-methyl-1H-pyrazole-3-carboxylate (1 eq, 39 mg, 0.072 mmol) and lithium hydroxide (3 eq, 5.2 mg, 0.215 mmol) was heated at 65° C. in tetrahydrofuran (3 mL) and water (3 mL) for 16 h. The reaction was quenched with a small amount of 10% HCl. The reaction was concentrated in vacuo. The crude reaction material was then purified by silica gel column chromatography using 0-10% methanol/dichloromethane with 1% acetic acid to yield 1-(2,4-dichlorophenyl)-5-[4-(dimethylamino)phenyl]-4-methyl-1H-pyrazole-3-carboxylic acid (11 mg, 39%). 1H NMR (300 MHz, CHLOROFORM-d) d ppm 2.36 (s, 3H) 2.84-3.05 (m, 6H) 6.60 (d, J=7.35 Hz, 2H) 6.97 (d, J=7.44 Hz, 2H) 7.20-7.37 (m, 2H) 7.42 (br. s., 1H)

Workup

  1. customThe reaction was quenched with a small amount of 10% HCl
  2. concentrationThe reaction was concentrated in vacuo
  3. customThe crude reaction material
  4. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ef77413860344ebf995ed8385b76e354
Source dataset
uspto-grants-2015_09
Patent number
US09133128B2

Reaction notes

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