1-Naphthaldehyde → 3-[1-Naphthalen-1-yl-methylidene]-imidazo[1,2-a]pyridin-2-one

HRID 215966Notes

Reaction equation

HRID 215966 reaction equation
Br.[N:2]1[C:3](=[O:11])[CH2:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12.[C:12]1([CH:22]=O)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>C(O)C>[C:12]1([CH:22]=[C:4]2[N:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]3=[N:2][C:3]2=[O:11])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 61951-NaphthaldehydeHCID 44121307Imidazo[1,2-a]pyridin-2(3H)-one--hydrogen bromide (1/1)

Product 1

HCID 686995473-[1-Naphthalen-1-yl-methylidene]-imidazo[1,2-a]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1 g (4.7 mmol) of imidazo[1,2-a]pyridin-2-one hydrobromide salt and 726 mg (4.7 mmol) of 1-naphthaldehyde in 20 mL of ethanol is heated at reflux for 1 h and then cooled to room temperature. The precipitate is collected. The isolated solid is suspended in 40 mL of 2M potassium carbonate solution and the resulting mixture is stirred for 48 h at room temperature. The precipitated solid is collected and washed with water to give the desired compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 h
  3. customThe precipitate is collected
  4. customThe precipitated solid is collected
  5. washwashed with water

Sources & evidence

ORD record
ord-f0f06ba9212746fab22dcc4750bb68b5
Source dataset
uspto-grants-2012_06
Patent number
US08193214B2

Reaction notes

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