Methane → HCID 15617194, compound

HRID 2351635Notes

Reaction equation

HRID 2351635 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:14](=O)[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2].C>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:24])[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:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:2]

Participants

4

Reactant 2

HCID 297MethaneHCID 14390491HCID 14390491, compound

Product 1

HCID 15617194HCID 15617194, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid N-[3-[(4-methoxybenzoyl)amino]-2-pyridinyl]glycine ethyl ester, 12.8 g (0.039 mole) was heated in glass in a Wood's metal bath at 210°-220° C. for 6 minutes. The residue was dissolved in methylene chloride, treated with charcoal, and filtered through a Celite pad. The filtrate (dark orange) was treated with Florisil® to give a pale orange filtrate. The filtrate was evaporated to a solid, which was recrystallized from tetrahydrofuran-petroleum ether. The solid was collected, washed with tetrahydrofuran-petroleum ether and dried under high vacuum at 50° C. overnight to give 3.58 g (29.5%) of title compound, mp 107°-8° C.

Workup

  1. filtrationfiltered through a Celite pad
  2. additionThe filtrate (dark orange) was treated with Florisil®
  3. customto give a pale orange filtrate
  4. customThe filtrate was evaporated to a solid, which
  5. customwas recrystallized from tetrahydrofuran-petroleum ether
  6. customThe solid was collected
  7. washwashed with tetrahydrofuran-petroleum ether
  8. customdried under high vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-ea759696ae894839ab9c087efdeb53ff
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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