HCID 178524561, compound → HCID 178524560, compound

HRID 878494Notes

Reaction equation

HRID 878494 reaction equation
C([C:4]1[CH:5]=[N:6][N:7]([C:10]2[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12][N:11]=2)[C:8]=1[OH:9])(O)=O>Cl>[OH:9][C:8]1[N:7]([C:10]2[CH:15]=[C:14]([CH:13]=[CH:12][N:11]=2)[C:16]([OH:18])=[O:17])[N:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 178524561HCID 178524561, compound

Product 1

HCID 178524560HCID 178524560, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-(4-carboxy-5-hydroxy-1H-pyrazol-1-yl)pyridine-4-carboxylic acid (1.7 g, 6.8 mmol) in conc. HCl (50 mL) was heated at 90° C. for 2 h. The reaction mixture was cooled, extracted with EtOAc (200 mL), and washed with water and brine. The organic phase was dried, concentrated, and recrystallized from EtOH to afford the title compound (230 mg, 47%) as a yellow solid. 1H NMR (400 MHz, CD3OD): δ 4.86 (1H, s), 7.68 (1H, s), 7.80 (1H, d, J=5.2 Hz), 8.60 (1H, d, J=1.6 Hz), 8.73 (1H, br). [M+H] Calc'd for C9H7N3O3, 206; Found, 206.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc (200 mL)
  3. washwashed with water and brine
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-9423a485a42a4e44aa2b574f81c2c439
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

Loading…