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

HRID 1447063Notes

Reaction equation

HRID 1447063 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.[OH2:20].[OH-:21].[K+]>Cl>[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:21])=[O:20])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium Hydroxide2×HCID 12918954HCID 12918954, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 422 g (1.67 mol) of the above nitrile and 3650 mol 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 hydrochloric acid. The solid is filtered, suspended in 8 L of water and filtered. The solid is washed with methanol and finally ethyl acetate and dried at 60° to give 328 g of the title compound; mp>314°-316° dec.

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 methanol and finally ethyl acetate
  8. customdried at 60°

Sources & evidence

ORD record
ord-30bf5065d0344ca7b1ce3b15fef0e850
Source dataset
uspto-grants-1982_02
Patent number
US04315014

Reaction notes

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