gamma-Octalactone → 4-hydroxy-3-(2-hydroxyhexyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

HRID 2118739Notes

Reaction equation

HRID 2118739 reaction equation
[C:1]1([NH:7][C:8]2[N:17]=[CH:16][CH:15]=[CH:14][C:9]=2[C:10]([O:12]C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][CH2:19][CH2:20][CH2:21][CH:22]1[O:27][C:25](=[O:26])[CH2:24][CH2:23]1.CC(C)([O-])C.[K+]>[OH-].[Na+]>[OH:12][C:10]1[C:9]2[C:8](=[N:17][CH:16]=[CH:15][CH:14]=2)[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:25](=[O:26])[C:24]=1[CH2:23][CH:22]([OH:27])[CH2:21][CH2:20][CH2:19][CH3:18]

Participants

5

Reactant 3

HCID 7704gamma-OctalactoneHCID 10998755Methyl 2-anilinopyridine-3-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 547178204-hydroxy-3-(2-hydroxyhexyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of methyl 2-phenylaminonicotinate (5 g.), gamma-octanoic lactone (10 g.) and potassium t-butoxide (7.5 g.) was stirred in a nitrogen atmosphere and heated to 95° C. where it was held for 6 hrs. After cooling, the mixture was poured into 5% NaOH (200 ml.) and stirred overnight. Acidification to pH 4.6 yielded an oil, which was extracted with ether, washed with water, dried (Na2SO4), filtered, and evaporated to a small volume. Hexane was added until turbidity was noticed, and the mixture was allowed to stand for about 5 hrs. The solid was filtered off and recrystallized from CH2Cl2 /isopropanol/isopropyl ether to produce the desired product, m.p. 184°-186° C.

Workup

  1. temperatureAfter cooling
  2. stirringstirred overnight
  3. customAcidification to pH 4.6 yielded an oil, which
  4. extractionwas extracted with ether
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated to a small volume
  9. additionHexane was added until turbidity
  10. waitto stand for about 5 hrs
  11. filtrationThe solid was filtered off
  12. customrecrystallized from CH2Cl2 /isopropanol/isopropyl ether

Sources & evidence

ORD record
ord-2cd1a0e8b0a4491ca60120a9bc71dd5b
Source dataset
uspto-grants-1987_07
Patent number
US04680298

Reaction notes

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