Sodium Bicarbonate → HCID 58523918, compound

HRID 2422676Notes

Reaction equation

HRID 2422676 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([OH:11])=[O:10])[C:4]=1[N+:12]([O-])=O.C(=O)([O-])O.[Na+].[H][H]>[C].[Pd].O>[NH2:12][C:4]1[C:5]([C:9]([OH:11])=[O:10])=[N:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 67246125HCID 67246125, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58523918HCID 58523918, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

4-Methoxy-3-nitropyridine-2-carboxylic acid (1.35 g, 6.81 mmol), sodium hydrogencarbonate (690 mg, 817 mmol), water (10 mL) and 10% palladium-carbon (135 mg) were stirred in a hydrogen atmosphere at room temperature for 24 hours. The reaction solution was filtered through Celite, the Celite was washed with water and methanol, and the mother liquid was concentrated. 2 N hydrochloric acid was added to the resulting residue, and the solution was controlled to have a pH of 1. The reaction solution was stirred at 0° C. for 1 hour, and the resulting pale gray solid was taken out through filtration and dried to obtain the intended compound (940 mg, 56%).

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washthe Celite was washed with water and methanol
  3. concentrationthe mother liquid was concentrated
  4. addition2 N hydrochloric acid was added to the resulting residue
  5. filtrationthe resulting pale gray solid was taken out through filtration
  6. customdried

Sources & evidence

ORD record
ord-5a5ea8f0849b41d2b82796bc27751d7e
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

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