HCID 22014403, compound → HCID 22014394, compound

HRID 1532765Notes

Reaction equation

HRID 1532765 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N+:13]([O-])=O)=[C:7]([O:9][CH2:10][O:11][CH3:12])[CH:8]=1)#[N:2].[H][H]>[Pd].C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH2:13])=[C:7]([O:9][CH2:10][O:11][CH3:12])[CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 22014403HCID 22014403, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22014394HCID 22014394, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-cyano- 1 -methoxymethyloxy-2-nitrobenzene (0.5 g, 2.4 mmol) and 10% palladium on carbon (.05 g) in ethyl acetate (50 mL) was stirred at rt under 1 atm of hydrogen for 72 h. The mixture was filtered through Celite to remove the palladium and the residue was chromatographed on silica gel (eluting with 25% ethylacetate/hexane) to afford the title compound (250 mg, 58%). MS(ES+) m/e 179 [M+H]+

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customto remove the palladium
  3. customthe residue was chromatographed on silica gel (eluting with 25% ethylacetate/hexane)

Sources & evidence

ORD record
ord-5da994ea9cd94c57acfa7c96b0fc6c2b
Source dataset
uspto-grants-2001_03
Patent number
US06204294B1

Reaction notes

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