Gamma-Valerolactone → HCID 54717823, compound

HRID 649566

Reaction equation

HRID 649566 reaction equation
[C:1]1(=[O:7])[O:6][CH:4]([CH3:5])[CH2:3][CH2:2]1.[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]2[N:27]=[CH:26][CH:25]=[CH:24][C:18]=2[C:19](OCC)=[O:20])[CH:12]=[CH:13][C:14]=1[Cl:15].CC(C)([O-])C.[K+].[OH-].[K+]>>[Cl:8][C:9]1[CH:10]=[C:11]([N:16]2[C:17]3[C:18](=[CH:24][CH:25]=[CH:26][N:27]=3)[C:19]([OH:20])=[C:2]([CH2:3][CH:4]([OH:6])[CH3:5])[C:1]2=[O:7])[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

5

Reactant 4

HCID 7921Gamma-ValerolactoneHCID 14797Potassium HydroxideHCID 20141561HCID 20141561, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54717823HCID 54717823, compound

Conditions

Temperature
110 °C

Procedure

A stirred mixture of gamma-valerolactone (40 g.), ethyl 2-(3,4-dichlorophenylamino)-nicotinate (20 g.) and potassium t-butoxide (30 g.) was warmed in an atmosphere of nitrogen to 110° C. and kept there for 5 hr. After cooling somewhat the product was poured into 1000 ml. of 5% KOH solution and was allowed to stir overnight. The basic solution was extracted with ether (2×500 ml.) and the aqueous solution was acidified to pH 5 with conc. HCl. The solid was filtered off, washed with water, dried in air then recrystallized from methanol/charcoal to yield the desired product, m.p. 232°-234° C.

Workup

  1. temperatureAfter cooling somewhat the product
  2. additionwas poured into 1000 ml
  3. extractionThe basic solution was extracted with ether (2×500 ml.)
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. customdried in air
  7. customthen recrystallized from methanol/charcoal

Sources & evidence

ORD record
ord-4e261e8176814b56b37d4c9bd0933b4d
Source dataset
uspto-grants-1988_04
Patent number
US04740511

Linked notes

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