4-Hydroxybenzaldehyde → HCID 22344627, compound

HRID 1070050Notes

Reaction equation

HRID 1070050 reaction equation
Cl.[Cl:2][C:3]1[N:8]2[CH:9]=[C:10]([CH2:12]Cl)[N:11]=[C:7]2[CH:6]=[CH:5][CH:4]=1.[OH:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:2][C:3]1[N:8]2[CH:9]=[C:10]([CH2:12][O:14][C:15]3[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=3)[N:11]=[C:7]2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 223446015-Chloro-2-(chloromethyl)imidazo(1,2-a)pyridine hydrochloride

Product 1

HCID 22344627HCID 22344627, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine hydrochloride (3.00 g), 4-hydroxybenzaldehyde (1.81 g), potassium carbonate (6.14 g) and N,N-dimethylformamide (30 ml) was stirred at room temperature for 15 hours, poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate-hexane to obtain 4-(5-chloroimidazo[1,2-a]pyridin-2-ylmethoxy)benzaldehyde (3.55 g, yield 98%) as colorless crystals. m.p. 126-130° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe remaining crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0c0c6051227c4266a714098826261d13
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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