Methane → HCID 14390463, compound

HRID 2072957Notes

Reaction equation

HRID 2072957 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][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2].C.C(Cl)[Cl:27]>C(O)(C)C>[ClH:27].[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][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])[CH3:2]

Participants

5

Reactant 3

HCID 297MethaneHCID 6344DichloromethaneHCID 14390493HCID 14390493, compound

Product 1

HCID 14390463HCID 14390463, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Solid N-[3-[(2-methoxybenzoyl)amino]-2-pyridinyl]glycine ethyl ester, 13.75 g (0.042 mole) was heated in glass in a Wood's metal bath at 210°-20° C. for 2 minutes, then at 215°-20° C. for 2 minutes. The residue was dissolved in methylene chloride, treated with activated charcoal, and filtered through a Celite pad. The filtrate (dark orange) was treated with Florisil® to give a dark filtrate, which was evaporated to give an oil. The oil was dissolved in isopropyl alcohol, filtered and the filtrate acidified with methanolic hydrogen chloride and diluted with isopropyl ether. The crystalline crop was collected, washed with isopropyl etherisopropyl alcohol (minimum), and dried under high vacuum at room temperature overnight to give 1.6 g (11%) of title compound, mp 177°-80° C.

Workup

  1. filtrationfiltered through a Celite pad
  2. additionThe filtrate (dark orange) was treated with Florisil®
  3. customto give a dark filtrate, which
  4. customwas evaporated
  5. customto give an oil
  6. filtrationfiltered
  7. additiondiluted with isopropyl ether
  8. customThe crystalline crop was collected
  9. washwashed with isopropyl etherisopropyl alcohol (minimum)
  10. customdried under high vacuum at room temperature overnight

Sources & evidence

ORD record
ord-6c7b2592b391481f88a3d9060da27640
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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