HCID 19102558, compound → HCID 15229160, compound

HRID 1646486Notes

Reaction equation

HRID 1646486 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:8]=2[CH:9]=O)=[C:4]([N+:19]([O-])=O)[CH:3]=1.[H][H]>O1CCCC1.[Ni]>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[O:6][C:7]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:8]=3[CH2:9][NH:19][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 19102558HCID 19102558, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15229160HCID 15229160, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5.00 g of 2-(4-chloro-2-nitrophenoxy)-5-methoxybenzaldehyde, prepared as described above in Example 1, in 50 mL of tetrahydrofuran (THF) was shaken in a Parr hydrogenator at 5 psi hydrogen with Raney nickel at 25° C. for 5 hours. The catalyst was filtered from the reaction and the solution evaporated in vacuo. The crude product was purified by column chromatography in the manner described by Still et al., "A Rapid Chromatographic Technique for Preparative Separations with Moderate Resolution," J. Org. Chem, 43, 2923 (1978), through silica gel 60 using hexane:ethyl acetate (2:1) to yield 2.08 g (48.9%) of product as a white solid. Melting Point: 111°-113° C.

Workup

  1. filtrationThe catalyst was filtered from the reaction
  2. customthe solution evaporated in vacuo
  3. customThe crude product was purified by column chromatography in the manner

Sources & evidence

ORD record
ord-923716a67b0f40ccba894837f3ec9fa5
Source dataset
uspto-grants-1993_01
Patent number
US05180720

Reaction notes

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