Triethylamine → HCID 14390520, compound

HRID 2351606Notes

Reaction equation

HRID 2351606 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][CH2:11][CH:12]([OH:14])[CH3:13])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.C(N(CC)CC)C>[Pd].O1CCCC1>[ClH:15].[OH:14][CH:12]([CH3:13])[CH2:11][NH:10][C:5]1[C:4]([NH:1][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][C:16]([Cl:15])=[CH:17][CH:18]=2)=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 156171811-[(3-Nitro-2-pyridinyl)amino]-2-propanol

Product 1

HCID 14390520HCID 14390520, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-[(3-nitro-2-pyridinyl)amino]-2-propanol (9.9 g, 0.05 mole) and 5% palladium on carbon (1.0 g) in 150 ml of tetrahydrofuran was hydrogenated in a glass Parr apparatus for 1/2 hour. The mixture was dried over magnesium sulfate and filtered through a Celite pad to give a colorless filtrate. The p-chlorobenzoyl chloride (8.79 g, 0.05 mole) and triethylamine (6.98 ml, 0.05 mole) were added dropwise to the stirred filtrate at 12°-15° C. (ice bath). The reaction mixture was allowed to warm to ambient temperature overnight. The reaction mixture was filtered, and the filtrate was evaporated to dryness. The residue was recrystallized from isopropyl alcohol and water. The solid was collected by filtration, then treated with boiling methanol. The insoluble solid was collected by filtration, and the filtrate was evaporated to dryness, azeotroped with benzene, and dried under high vacuum. The residue was partitioned between water and methylene chloride. The methylene chloride was extracted with 5% potassium hydroxide and water. The methylene chloride layer was dried, filtered, and evaporated to a foam. A 1.5-g sample was dissolved in ethyl acetate, acidified with ethereal and methanolic hydrogen chloride, and seeded. The crystalline solid was collected by filtration, washed with ethyl acetate, and dried under high vacuum to give 1.2 g of solid, mp 178°-180° C.

Workup

  1. dry with materialThe mixture was dried over magnesium sulfate
  2. filtrationfiltered through a Celite pad
  3. customto give a colorless filtrate
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate was evaporated to dryness
  6. customThe residue was recrystallized from isopropyl alcohol and water
  7. filtrationThe solid was collected by filtration
  8. additiontreated with boiling methanol
  9. filtrationThe insoluble solid was collected by filtration
  10. customthe filtrate was evaporated to dryness
  11. customazeotroped with benzene
  12. customdried under high vacuum
  13. customThe residue was partitioned between water and methylene chloride
  14. extractionThe methylene chloride was extracted with 5% potassium hydroxide and water
  15. dry with materialThe methylene chloride layer was dried
  16. filtrationfiltered
  17. customevaporated to a foam
  18. dissolutionA 1.5-g sample was dissolved in ethyl acetate
  19. filtrationThe crystalline solid was collected by filtration
  20. washwashed with ethyl acetate
  21. customdried under high vacuum

Sources & evidence

ORD record
ord-cc9f8d0eeeca4cdc918d66b621de9f71
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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