HCID 18419446, compound → HCID 15887618, compound

HRID 377105Notes

Reaction equation

HRID 377105 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14](=[O:24])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N+:21]([O-])=O)=[CH:9][CH:8]=2)=[C:4]([CH3:27])[CH:3]=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:14]([NH:13][C:10]1[CH:11]=[N:12][C:7]([O:6][C:5]2[CH:25]=[CH:26][C:2]([Cl:1])=[CH:3][C:4]=2[CH3:27])=[CH:8][CH:9]=1)=[O:24]

Participants

5

Reactant 2

HCID 18419446HCID 18419446, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15887618HCID 15887618, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

N-(6-(4-chloro-2-methyl-phenoxy)-pyridin-3-yl)-2-nitro-benzamide (301 mg, 0.7 mmol) was dissolved in 95% ethanol (4 mL) and treated with 20% palladium hydroxide on carbon (Pearlman's catalyst, 50 mg) and subjected to a hydrogen atmosphere (40 psi) for 2 hours. The catalyst was removed by filtration and the solvents were removed in vacuo. The product was purified by chromatography on SiO2 using 1:1 ethyl acetate/hexanes as eluent. MS (m/z) 353/355 (M+H)+ ; C19H16N3O2Cl requires 353.8.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvents were removed in vacuo
  3. customThe product was purified by chromatography on SiO2 using 1:1 ethyl acetate/hexanes as eluent

Sources & evidence

ORD record
ord-b5809eebe80844459543c0d7a41a7b8e
Source dataset
uspto-grants-2000_02
Patent number
US06022884

Reaction notes

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