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

HRID 2413650Notes

Reaction equation

HRID 2413650 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.CC([O-])(C)C.[K+].[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

6

Reactant 4

HCID 795ImidazoleHCID 14798Sodium HydroxideHCID 8270310-Chloro-9-anthraldehydeHCID 23665647Potassium tert-butoxide

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 mol) and DMF (300 mL) was warmed to 55° and treated with KOtBu (MCB, 7.9 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. filtrationThe precipitate was filtered
  2. customchromatographed on a plug of SiO2 (500 g)
  3. washinitial eluting solvent
  4. customto remove
  5. washThe yellow product band was then eluted with EtOAc (2 L)
  6. customto yield
  7. customafter removal of solvent
  8. customdrying

Sources & evidence

ORD record
ord-f2103989d4a344a7b88d7c224af023e9
Source dataset
uspto-grants-1988_01
Patent number
US04719049

Reaction notes

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