HCID 90460321, compound → HCID 90460782, compound

HRID 2202107Notes

Reaction equation

HRID 2202107 reaction equation
[OH:1][CH2:2][C:3]1[N:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[N:6]=[N:5][CH:4]=1>ClCCl.O=[Mn]=O>[CH:2]([C:3]1[N:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[N:6]=[N:5][CH:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 90460321HCID 90460321, compound

Product 1

HCID 90460782HCID 90460782, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]benzonitrile (225 mg, 1.12 mmol, 1.00 equiv) and MnO2 (1958 mg, 22.52 mmol, 20.04 equiv) in dichloromethane (20 mL) was stirred at room temperature overnight. The solid material was removed by filtration. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with 0-50% of ethyl acetate in petroleum ether to give 110 mg (49%) of 4-(5-formyl-1H-1,2,3-triazol-1-yl)benzonitrile as a white solid. 1H NMR (400 MHz, DMSO-d6) δ: 9.96 (s, 1H), 8.70 (s, 1H), 8.15 (d, J=8.0 Hz, 2H), 7.97 (d, J=8.0 Hz, 2H) ppm.

Workup

  1. customThe solid material was removed by filtration
  2. concentrationThe filtrate was concentrated under vacuum
  3. customthe residue was purified on a silica gel column
  4. washeluted with 0-50% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-e837168141974d12bb6b2ae984ac99de
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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