Methane → HCID 15617179, compound

HRID 2351631Notes

Reaction equation

HRID 2351631 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=O)=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2].C>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:12]2[N:13]=[C:14]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH3:2]

Participants

4

Reactant 2

HCID 297MethaneHCID 14390489HCID 14390489, compound

Product 1

HCID 15617179HCID 15617179, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid N-[3-[(2-pyridinylcarbonyl)amino]-2-pyridinyl]glycine ethyl ester (21.9 g, 0.069 mole) was heated in glass at 210°-220° C. using a heating mantle for 71/2 minutes. The residue was dissolved in methylene chloride, treated with 25.6 g of charcoal, and filtered through a Celite pad. The filtrate was evaporated to a dark residue, which was taken up in ethyl acetate and filtered to remove an insoluble brown solid. The concentrated ethyl acetate filtrate was applied to a silica gel column (400 g) and eluted with ethyl acetate. The appropriate fractions were combined and evaporated to a solid, which was placed under high vacuum for several hours. The solid residue (6.9 g) was recrystallized from ethanol-water and refrigerated overnight. The crystalline precipitate was filtered, washed with water, and dried under high vacuum at room temperature overnight to give 6.34 g of title compound (31%), mp 109°-111° C.

Workup

  1. custom2 minutes
  2. filtrationfiltered through a Celite pad
  3. customThe filtrate was evaporated to a dark residue, which
  4. filtrationfiltered
  5. customto remove an insoluble brown solid
  6. washeluted with ethyl acetate
  7. customevaporated to a solid, which
  8. waitwas placed under high vacuum for several hours
  9. customThe solid residue (6.9 g) was recrystallized from ethanol-water and refrigerated overnight
  10. filtrationThe crystalline precipitate was filtered
  11. washwashed with water
  12. customdried under high vacuum at room temperature overnight

Sources & evidence

ORD record
ord-4dc130cacd604218946f8fad0574a3fb
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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