Methanol → 4-(6-Methylimidazo[1,2-a]pyridin-2-yl)benzaldehyde

HRID 1590617Notes

Reaction equation

HRID 1590617 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]#N)=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.CO.[OH:21]S(O)(=O)=O>C1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH:17]=[O:21])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 7359124-(6-Methylimidazo[1,2-a]pyridin-2-yl)benzonitrile

Product 1

HCID 8210554-(6-Methylimidazo[1,2-a]pyridin-2-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.0 g of 6-methyl-2-(4'-cyanophenyl)imidazo[1,2-a]-pyridine in 20 ml dry benzene was treated with Dibal (5.5 ml of 1M solution). After stirring for 2-3 hrs, methanol 15 ml was added, followed by 10 ml of 10% H2SO4. The precipitate was filtered, dissolved in water and basified with 15% NaOH. The collected precipitate was recrystallized from ethanol. Yield 0.68 g (68%); mp 210°-211° C.

Workup

  1. filtrationThe precipitate was filtered
  2. dissolutiondissolved in water and basified with 15% NaOH
  3. customThe collected precipitate was recrystallized from ethanol

Sources & evidence

ORD record
ord-9cd1722affe942508d49bbc475a097a8
Source dataset
uspto-grants-1993_04
Patent number
US05204352

Reaction notes

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