Hydrochloric Acid → HCID 22099272, compound

HRID 1360359Notes

Reaction equation

HRID 1360359 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])(=O)[NH2:2].P(Cl)(Cl)(Cl)=O.Cl.[H][H]>C(O)C.[Pd]>[NH2:2][CH2:1][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 3366825-carbamoylpyridine-3-carboxylic acid2×HCID 178418361HCID 178418361, compound

Product 1

HCID 22099272HCID 22099272, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-carbamoyl-nicotinic acid (compound F3) (5.00 g) and phosphorus oxychloride (50 mL, 0.55 mol) is heated to 100° C. for 5 h. After usual workup the crude product is dissolved in ethanol acidified with hydrochloric acid and hydrogenated with the use of Pd/C (1.00 g, 5% Pd) at 4 bar hydrogen pressure for 16 h. After filtration of the catalyst, the mixture is evaporated, and the residue is treated with ethanol and extracted several times with chloroform.

Workup

  1. filtrationAfter filtration of the catalyst
  2. customthe mixture is evaporated
  3. additionthe residue is treated with ethanol
  4. extractionextracted several times with chloroform

Sources & evidence

ORD record
ord-712742a5ec7848f9a74f49cdd5eab32e
Source dataset
uspto-grants-2011_02
Patent number
US07879853B2

Reaction notes

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