Imidazole → 10-(1-H-Imidazol-1-yl)-9-anthracencarbaldehyde

HRID 1381786Notes

Reaction equation

HRID 1381786 reaction equation
Cl[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH:16]=[O:17])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.[OH-].[Na+]>CN(C=O)C>[N:18]1([C:2]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH:16]=[O:17])=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[CH:7]3)[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 14798Sodium HydroxideHCID 8270310-Chloro-9-anthraldehyde

Product 1

HCID 1337540910-(1-H-Imidazol-1-yl)-9-anthracencarbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 10-chloro-9-anthraldehyde (Aldrich, 15 g, 0.062 mol), imidazole (Aldrich, 10.2 g, 0.15 mmol) and DMF (300 mL) was warmed to 55° and treated with KotBu (MCB, 7.0 g, 0.07 mol) and stirred for 30 min. The reaction mixture was poured into 0.1N NaOH (1.5 L). The precipitate was filtered and then chromatographed on a plug of SiO2 (500 g) using CH2Cl2 (3 L) as the initial eluting solvent to remove starting material and byproducts. The yellow product band was then eluted with EtOAc (2 L) to yield, after removal of solvent and drying, 12.29 g (73%) of 10-(1H-imidazol-1-yl)-9-anthracenecarbaldehyde mp 194°-196°, (C, H, N), (EtOAc).

Workup

  1. additiontreated with KotBu (MCB, 7.0 g, 0.07 mol)
  2. filtrationThe precipitate was filtered
  3. customchromatographed on a plug of SiO2 (500 g)
  4. washinitial eluting solvent
  5. customto remove
  6. washThe yellow product band was then eluted with EtOAc (2 L)
  7. customto yield
  8. customafter removal of solvent
  9. customdrying

Sources & evidence

ORD record
ord-68d5c1bf23e34bb48a257124bfaaa781
Source dataset
uspto-grants-1989_02
Patent number
US04803221

Reaction notes

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