HCID 90460898, compound → HCID 90460323, compound

HRID 2202111Notes

Reaction equation

HRID 2202111 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)[CH: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)[CH:6]=[N:5][CH:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 90460898HCID 90460898, compound

Product 1

HCID 90460323HCID 90460323, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(5-(hydroxymethyl)-1H-imidazol-1-yl)benzonitrile (80 mg, 0.40 mmol, 1.00 equiv) and MnO2 (525 mg, 6.04 mmol, 15.04 equiv) in dichloromethane (10 mL) was refluxed for 1 h. The reaction was cooled to room temperature and the solid material was removed by filtration. The filtrate was concentrated under vacuum to give 55 mg (69%) of 4-(5-formyl-1H-imidazol-1-yl)benzonitrile as a white solid. 1H-NMR (300 MHz, CDCl3): δ 9.80 (s, 1H), 8.03 (s, 1H), 7.99-7.80 (m, 3H), 7.56-7.49 (m, 2H) ppm. LCMS (method D, ESI): RT=1.06 min, m/z=198.0 [M+H]+.

Workup

  1. temperaturewas refluxed for 1 h
  2. customthe solid material was removed by filtration
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-7b1b7a2232014a4cb889b9a9c3eb7eda
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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