Sodium Hydroxide → 2-(6-Methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid

HRID 902005Notes

Reaction equation

HRID 902005 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=2)=[N:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12)=[O:5])C.[OH-].[Na+]>CCO>[CH3:21][C:17]1[N:16]=[C:15]([C:7]2[C:6]([C:4]([OH:5])=[O:3])=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 597006232-(6-Methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester

Product 1

HCID 597006062-(6-Methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridine-3-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(6-methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester (0.18 g, 0.6 mmol) in EtOH (10 mL) is treated with a 2N NaOH solution (3 mL) and refluxed for 3 hours. The reaction is concentrated to a yellow solid and diluted with 1N HCl (30 mL). The aqueous is extracted with CH2Cl2 (3×10 mL) and the organic solution dried over Na2SO4. The solution is filtered and the solvent removed in vacuo to afford 0.152 g (94%) of desired product as a white solid. MS ES+ m/e 254.1 (M+1). UV (95% EtOH) λmax 284 nm (ε 23625), 244 nm (ε 24036). TOF MS ES+ exact mass calculated for C14H11N3O2 (p+1): m/z=254.0930. Found: 254.0919. Anal. Calcd for C14H11N3O2: C, 66.40; H, 4.38; N, 16.59. Found: C, 66.22; H, 4.42; N, 16.25.

Workup

  1. temperaturerefluxed for 3 hours
  2. concentrationThe reaction is concentrated to a yellow solid
  3. additiondiluted with 1N HCl (30 mL)
  4. extractionThe aqueous is extracted with CH2Cl2 (3×10 mL)
  5. dry with materialthe organic solution dried over Na2SO4
  6. filtrationThe solution is filtered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8cc0d94e98ec4cd5a5c20a0bd85fd285
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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