HCID 67515597, compound → HCID 67514925, compound

HRID 1468174Notes

Reaction equation

HRID 1468174 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=3)[N:13]=[N:12]2)[CH:5]=1>CO.O>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([C:14]2[N:13]=[N:12][N:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:24])=[O:2])[CH:15]=2)=[CH:21][CH:20]=1)#[N:23]

Participants

3

Reactant 1

HCID 67515597HCID 67515597, compound

Product 1

HCID 67514925HCID 67514925, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Add LiOH monohydrate (0.10 g, 2.40 mmol) to a suspension of 3-[4-(4-cyano-phenyl)-[1,2,3]triazol-1-ylmethyl]-benzoic acid methyl ester (0.50 g, 1.60 mmol) in 15 mL of a 4:1 MeOH-water mixture and stir at room temperature for 3 days. Concentrate the mixture to remove most of the MeOH, dilute with additional H2O and neutralize by the addition of 1N aqueous HCl. Isolate the resulting solid by filtration and dry to afford 0.45 g, 94% yield of 3-[4-(4-Cyano-phenyl)-[1,2,3]triazol-1-ylmethyl]-benzoic acid.

Workup

  1. concentrationConcentrate the mixture
  2. customto remove most of the MeOH
  3. additiondilute with additional H2O and neutralize by the addition of 1N aqueous HCl
  4. customIsolate the resulting solid
  5. filtrationby filtration
  6. customdry

Sources & evidence

ORD record
ord-f5683f3642cb4fa2a4b95e6777729636
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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