Acetic Acid → ethyl 6-oxo-1,2-dihydropyrazolo[3,4-b]pyridine-4-carboxylate

HRID 82020

Reaction equation

HRID 82020 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.[Na].[C:8](OCC)(=[O:17])[CH2:9][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=O.C(O)(=O)C>O>[CH2:15]([O:14][C:12]([C:10]1[C:6]2[CH:5]=[N:4][NH:3][C:2]=2[N:1]=[C:8]([OH:17])[CH:9]=1)=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 57351814Diethyl 2-oxosuccinate,sodium saltHCID 178418806HCID 178418806, compound

Product 1

HCID 178469358ethyl 6-oxo-1,2-dihydropyrazolo[3,4-b]pyridine-4-carboxylateYield 28.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
85 °C

Procedure

To a solution of 3-aminopyrazole (224 g, 2.7 mol) in water (1 L) were added a solution of diethyl oxalacetate sodium salt (567 g, 2.7 mol) in water (1.3 L) and then acetic acid in 4 portions (0.8 L). The reaction mixture was heated at 85° C. for 15 hours then cooled to room temperature and filtered. The precipitate was washed with water and then dried to afford the title compound as an orange solid (159 g, 28%). 1H NMR (250 MHz, DMSO): δ 1.35 (t, 3H), 4.36 (q, 2H), 6.69 (s, 1H), 8.16 (s, 1H).

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationfiltered
  3. washThe precipitate was washed with water
  4. customdried

Sources & evidence

ORD record
ord-e3eb65687a5b40aca63272abc8d1d7f7
Source dataset
uspto-grants-2014_09
Patent number
US08846712B2

Linked notes

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