6-Aminonicotinic acid → HCID 67273587, compound

HRID 600626Notes

Reaction equation

HRID 600626 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[Br:11][CH2:12][C:13](=O)[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15]>C1COCC1.C(O)C>[BrH:11].[C:14]([C:13]1[N:1]=[C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]2[CH:12]=1)(=[O:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 184966-Aminonicotinic acidHCID 125689113-Bromo-1-phenylpropane-1,2-dione

Product 1

HCID 67273587HCID 67273587, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

To a suspension of 0.33 g of 6-aminonicotinic acid in 5 mL of THF and 3 mL of ethanol is added a solution of 0.654 g of 3-bromo-1-phenylpropane-1,2-dione in 2 mL of THF. The reaction mixture is stirred at 45° C. for 16 hours and for 24 hours at 20° C., and then evaporated to dryness. The residue is taken up in dichloromethane and the solid is filtered off and washed with dichloromethane to give 0.78 g of 2-benzoylimidazo[1,2-a]pyridine-6-carboxylic acid hydrobromide in the form of a yellow solid.

Workup

  1. customevaporated to dryness
  2. filtrationthe solid is filtered off
  3. washwashed with dichloromethane

Sources & evidence

ORD record
ord-a705250289134b1d9e714d4881574492
Source dataset
uspto-grants-2011_03
Patent number
US07902219B2

Reaction notes

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