Methanol → HCID 14676658, compound

HRID 2351612Notes

Reaction equation

HRID 2351612 reaction equation
[CH3:1][N:2]([CH3:16])[C:3](=[O:15])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[N+:12]([O-])=[O:13].[CH3:17][OH:18].[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.C(N([CH2:34][CH3:35])CC)C>[Pd].O1CCCC1>[OH2:13].[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([N:12]([C:17](=[O:18])[C:35]2[CH:34]=[CH:28][C:20]([Cl:19])=[CH:21][CH:22]=2)[C:7]2[CH:8]=[N:9][CH:10]=[CH:11][C:6]=2[NH:5][CH2:4][C:3]([N:2]([CH3:16])[CH3:1])=[O:15])=[O:25])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 15617223HCID 15617223, compound

Product 1

HCID 14676658HCID 14676658, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N,N-dimethyl-2-[(3-nitro-4-pyridinyl)amino]-acetamide (11.0 g, 0.05 mole) and 5% palladium on carbon catalyst (1.1 g) in 250 ml of tetrahydrofuran was hydrogenated in a small Parr apparatus while heating at 50° C. The reaction mixture was heated with methanol and filtered through a Celite pad. The pad was washed with boiling methanol. The filtrate was evaporated to a solid. The solid was dissolved in acetonitrile (500 ml) and treated with p-chlorobenzoyl chloride (5.97 ml, 0.047 mole) and triethylamine (6.52 ml, 0.047 mole). The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was filtered and the filtrate was evaporated. The solid residue was partitioned between methylene chloride and water (2×). The methylene chloride layer was dried and evaporated to dryness. The residue was dissolved in ethyl acetate, treated with charcoal, filtered through Celite, and concentrated. A crystalline precipitate was collected by filtration, washed with isopropyl ether and dried at 50° C. under high vacuum to give 4.65 g of solids (40%), mp 175°-176° C.

Workup

  1. filtrationfiltered through a Celite pad
  2. washThe pad was washed with boiling methanol
  3. customThe filtrate was evaporated to a solid
  4. dissolutionThe solid was dissolved in acetonitrile (500 ml)
  5. filtrationThe reaction mixture was filtered
  6. customthe filtrate was evaporated
  7. customThe solid residue was partitioned between methylene chloride and water (2×)
  8. dry with materialThe methylene chloride layer was dried
  9. customevaporated to dryness
  10. dissolutionThe residue was dissolved in ethyl acetate
  11. additiontreated with charcoal
  12. filtrationfiltered through Celite
  13. concentrationconcentrated
  14. filtrationA crystalline precipitate was collected by filtration
  15. washwashed with isopropyl ether
  16. customdried at 50° C. under high vacuum

Sources & evidence

ORD record
ord-90d3ab89bcdb4b56827bbbc0982ce2ab
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

Loading…