Hydrochloric Acid → 6-(4-Aminophenyl)-1,2-dihydro-2-oxonicotinic acid

HRID 1447295Notes

Reaction equation

HRID 1447295 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13](=[O:19])[C:14](=[CH:17][CH:18]=2)[C:15]#N)=[CH:7][CH:6]=1)(=O)C.[OH-:20].[K+].Cl.[OH2:23]>>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13](=[O:19])[C:14](=[CH:17][CH:18]=2)[C:15]([OH:23])=[O:20])=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium Hydroxide2×HCID 12918954HCID 12918954, compound

Product 1

HCID 129189566-(4-Aminophenyl)-1,2-dihydro-2-oxonicotinic acid

Procedure

A suspension of 422 g (1.67 mol) of the above nitrile and 3650 ml of water containing 932 g of potassium hydroxide is heated at 105° for 40 hrs. The solution is cooled and acidified to pH 4.0 with 1360 ml of concentrated hydrochloric acid and 400 g of potassium hydroxide pellets are added with stirring. After filtration, the pH of the filtrate is adjusted to 4.5 with concentrated hyrochloric acid. The solid is filtered, suspended in 8 L of water and filtered. The solid is washed with mthanol and finally ethyl acetate and dried at 60° to give 328 g of the title compound; mp 314°-316° dec. ##STR21##

Workup

  1. temperatureis heated at 105° for 40 hrs
  2. temperatureThe solution is cooled
  3. additionare added
  4. filtrationAfter filtration
  5. filtrationThe solid is filtered
  6. filtrationfiltered
  7. washThe solid is washed with mthanol and finally ethyl acetate
  8. customdried at 60°

Sources & evidence

ORD record
ord-63f0a2a2a9e64c9c9ca9d0a8e5074596
Source dataset
uspto-grants-1982_02
Patent number
US04315858

Reaction notes

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