Pyridine → N-(7-Chloro-3-propanamidoquinoxalin-2-yl)hexanamide

HRID 1288221Notes

Reaction equation

HRID 1288221 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][C:14](=[O:17])[CH2:15][CH3:16])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([Cl:12])=[CH:7][CH:6]=2.N1C=CC=CC=1.[C:24](Cl)(=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O1CCCC1>[Cl:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]=[C:3]([NH:13][C:14](=[O:17])[CH2:15][CH3:16])[C:2]([NH:1][C:24](=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[N:11]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 67340Hexanoyl chlorideHCID 21504583HCID 21504583, compound

Product 1

HCID 21504581N-(7-Chloro-3-propanamidoquinoxalin-2-yl)hexanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 50 parts of 3-amino-6-chloro-2-propionamidoquinoxaline in 1000 parts of pyridine was cooled to 5° in an ice bath. A solution of 96 parts of hexanoyl chloride in 88 parts of tetrahydrofuran was added as quickly as possible with good cooling to prevent the temperature from rising above 25°. The reaction mixture was stirred for 10 minutes and then poured into 2500 parts of ice water. The yellow gum which separated was removed by filtration and washed with water and then dissolved in 2700 parts of methylene chloride. The methylene chloride solution was washed in succession with 1000 parts each of water, 5% aqueous hydrochloric acid, water, 10% aqueous sodium carbonate, and water. The methylene chloride solution was dried (MgSO4) and evaporated. The residue was recrystallized from 1:4 ethyl acetate-benzene, the solid filtered off, and washed with ether to yield 8 parts of 6-chloro-3-hexanamido-2-propionamidoquinoxaline, m.p. 158°-160°, as a colorless solid.

Workup

  1. temperaturewas cooled to 5° in an ice bath
  2. temperaturewith good cooling
  3. customfrom rising above 25°
  4. customThe yellow gum which separated
  5. customwas removed by filtration
  6. washwashed with water
  7. dissolutiondissolved in 2700 parts of methylene chloride
  8. washThe methylene chloride solution was washed in succession with 1000 parts each of water, 5% aqueous hydrochloric acid, water, 10% aqueous sodium carbonate, and water
  9. dry with materialThe methylene chloride solution was dried (MgSO4)
  10. customevaporated
  11. customThe residue was recrystallized from 1:4 ethyl acetate-benzene
  12. filtrationthe solid filtered off
  13. washwashed with ether

Sources & evidence

ORD record
ord-88601398403749cf9627ff60fb228e5b
Source dataset
uspto-grants-1976_10
Patent number
US03987171

Reaction notes

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