Acetic Acid → HCID 21496115, compound

HRID 1730649Notes

Reaction equation

HRID 1730649 reaction equation
[C:1]([NH:4][C:5]1[C:6]([CH3:22])=[C:7]2[C:12](=[N:13][C:14]=1[CH3:15])[NH:11][C:10](=[O:16])[C:9]([C:17]([O:19]CC)=[O:18])=[CH:8]2)(=[O:3])[CH3:2].[OH-].[K+].C(O)(=O)C>O>[C:1]([NH:4][C:5]1[C:6]([CH3:22])=[C:7]2[C:12](=[N:13][C:14]=1[CH3:15])[NH:11][C:10](=[O:16])[C:9]([C:17]([OH:19])=[O:18])=[CH:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 21496101HCID 21496101, compound

Product 1

HCID 21496115HCID 21496115, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 6-acetamido-5,7-dimethyl-1,8-naphthyridin-2(1H)-one-3-carboxylate (321 mg., 1 mmole), prepared as described in Example 28, is dissolved in water (2 ml.) to which has been added 40% w/w potassium hydroxide solution (0.28 ml.) and the clear solution heated on a steam bath for 2 hours. The solution is cooled and acidified to pH 5.5 with dilute acetic acid giving initially a gelatinous precipitate which becomes denser and more crystalline on standing at ambient temperature. The product is collected, washed with water and dried yielding 195 mg. (66%) of product, m.p. 305° C. (dec.). The product is purified by dissolving in dilute ammonium hydroxide solution, treating with charcoal and reprecipitating with acetic acid with no change in melting point.

Workup

  1. temperaturethe clear solution heated on a steam bath for 2 hours
  2. temperatureThe solution is cooled
  3. customon standing at ambient temperature
  4. customThe product is collected
  5. washwashed with water
  6. customdried
  7. customyielding 195 mg
  8. customThe product is purified
  9. dissolutionby dissolving in dilute ammonium hydroxide solution
  10. additiontreating with charcoal
  11. customreprecipitating with acetic acid with no change

Sources & evidence

ORD record
ord-e941e44f3ba24abbacf269fc44a7dc4b
Source dataset
uspto-grants-1976_11
Patent number
US03993656

Reaction notes

Loading…