Hydrochloric Acid → 2-Amino-5-(1-ethyl-6-oxo-1,6-dihydro-3-pyridinyl)-6-(2-furyl)nicotinic acid

HRID 353228Notes

Reaction equation

HRID 353228 reaction equation
[OH-:1].[Na+].[NH2:3][C:4]1[N:11]=[C:10]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)[C:9]([C:17]2[CH:22]=[CH:21][C:20](=[O:23])[N:19]([CH2:24][CH3:25])[CH:18]=2)=[CH:8]C=1C#N.Cl.[CH2:27]([OH:29])[CH3:28]>>[NH2:3][C:4]1[N:11]=[C:10]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)[C:9]([C:17]2[CH:22]=[CH:21][C:20](=[O:23])[N:19]([CH2:24][CH3:25])[CH:18]=2)=[CH:8][C:28]=1[C:27]([OH:1])=[O:29]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 129921352-Amino-5-(1-ethyl-6-oxo-1,6-dihydro-3-pyridinyl)-6-(2-furyl)nicotinonitrile

Product 1

HCID 129921372-Amino-5-(1-ethyl-6-oxo-1,6-dihydro-3-pyridinyl)-6-(2-furyl)nicotinic acidYield 98%

Procedure

Ethanol (5 mL) and 5 N aqueous sodium hydroxide (10 mL) were added to 2-amino-5-(1-ethyl-6-oxo-1,6-dihydro-3-pyridinyl)-6-(2-furyl)nicotinonitrile (308 mg, 1.01 mmol), followed by heating under reflux for 4 hours. After cooling as it was, the reaction solution was neutralized with 5 N hydrochloric acid. The resulting solid was collected by filtration and then washed with water, to give the title compound (320 mg, 98%) as a yellow solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling as it
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-fdde1940ed434b768344fc3d8bf99046
Source dataset
uspto-grants-2004_06
Patent number
US06750232B2

Reaction notes

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