Delta-Valerolactone → HCID 54716548, compound

HRID 649565Notes

Reaction equation

HRID 649565 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:20]=[CH:19][CH:18]=[CH:17][C:11]=2[C:12]([O:14]CC)=O)=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].[OH-].[K+].[C:29]1(=[O:35])[O:34][CH2:33][CH2:32][CH2:31][CH2:30]1>>[OH:14][C:12]1[C:11]2[C:10](=[N:20][CH:19]=[CH:18][CH:17]=2)[N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:33](=[O:34])[C:32]=1[CH2:31][CH2:30][CH2:29][OH:35]

Participants

5

Reactant 4

HCID 10953Delta-ValerolactoneHCID 14797Potassium HydroxideHCID 14222104Ethyl 2-(4-methoxyanilino)pyridine-3-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 54716548HCID 54716548, compound

Conditions

Temperature
100 °C

Procedure

A mixture of delta-valerolactone (120 ml.), ethyl 2-(4-methoxyphenylamino)nicotinate (12 g.) and potassium t-butoxide (24 g.) was stirred and heated in an atmosphere of nitrogen to 100° C. for 2 hrs. After cooling, the mixture was poured into 1000 ml. of 5% KOH solution and stirred overnight. The aqueous solution was extracted with ether (2×250 ml.) which was discarded. The aqueous solution was then acidified to pH 4.5 with conc. HCl. The product was filtered off, washed with water, dried in air and recrystallized from CHCl3 /isopropanol to yield the desired product, m.p. 229°-231° C.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture was poured into 1000 ml
  3. extractionThe aqueous solution was extracted with ether (2×250 ml.) which
  4. filtrationThe product was filtered off
  5. washwashed with water
  6. customdried in air
  7. customrecrystallized from CHCl3 /isopropanol

Sources & evidence

ORD record
ord-e0428c80de64480faf4825a14bdf286b
Source dataset
uspto-grants-1988_04
Patent number
US04740511

Reaction notes

Loading…