Sodium Hydroxide → 2-(3-Chloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid sodium salt

HRID 229442Notes

Reaction equation

HRID 229442 reaction equation
[OH-].[Na+:2].C[O:4][C:5]([C:7]1[CH:12]=[CH:11][N:10]2[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[N:15]=[C:9]2[CH:8]=1)=[O:6]>C1COCC1.CO>[Na+:2].[Cl:22][C:18]1[CH:17]=[C:16]([C:14]2[N:15]=[C:9]3[CH:8]=[C:7]([C:5]([O-:6])=[O:4])[CH:12]=[CH:11][N:10]3[CH:13]=2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57758482Methyl 2-(3-chlorophenyl)imidazo[1,2-a]pyridine-7-carboxylate

Product 1

HCID 688408032-(3-Chloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid sodium salt

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (1 mL, 2N) was added to a solution of 2-(3-chloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (122 mg, 0.43 mmol) in THF (4 mL) and methanol (1 mL). The mixture was stirred for 4 hours then evaporated to dryness. Ethyl acetate was added and removed in vacuo three times to afford crude 2-(3-chloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid sodium salt (quantitative yield) which was used without further purification. m/z (M+H)=273.1.

Workup

  1. customthen evaporated to dryness
  2. additionEthyl acetate was added
  3. customremoved in vacuo three times

Sources & evidence

ORD record
ord-bbabddb63dcc48d7a4311ee72b3b450a
Source dataset
uspto-grants-2009_07
Patent number
US07563797B2

Reaction notes

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