HCID 22612095, compound → HCID 22612137, compound

HRID 844043Notes

Reaction equation

HRID 844043 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[O:7][C:8]1[N:24]=[CH:23][CH:22]=[CH:21][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])=[O:11])([O-])=O.[H][H]>CO.O1CCCC1.O=[Pt]=O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[O:7][C:8]1[N:24]=[CH:23][CH:22]=[CH:21][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])=[O:11]

Participants

6

Reactant 2

HCID 22612095HCID 22612095, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22612137HCID 22612137, compound

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-Nitro-phenoxy)-N-(2-chloro-benzyl)-nicotinamide (0.530 g 1.38 mmole) in methanol (15 ml) and tetrahydrofuran (20 ml) was added 10% PtO2 (0.0.50 g). This was shaken under 35 psi hydrogen for 1 hour 40 minutes. The catalyst was removed by filtration, and the solution was concentrated to give an oil that was purified by chromatography on silica gel eluting with 2.5% methanol/methylene chloride. Recrystalization from ethyl acetate/hexane gave crystals. (0.327 g). M.P. 101-103° C.; Anal. calcd. for C19H16N3O2Cl: C, 64.5; H, 4.56; N, 11.88. Found: C, 64.15; H,4.07; N, 11.80.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solution was concentrated
  3. customto give an oil that
  4. customwas purified by chromatography on silica gel eluting with 2.5% methanol/methylene chloride
  5. customRecrystalization from ethyl acetate/hexane
  6. customgave crystals

Sources & evidence

ORD record
ord-844dde14f94246c0a8dd855bfb08b328
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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