HCID 15229161, compound → HCID 15229162, compound

HRID 1198385Notes

Reaction equation

HRID 1198385 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[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]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:8]=3[CH2:9][NH:19][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 15229161HCID 15229161, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15229162HCID 15229162, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3.50 g of 2-(4-chloro-2-nitrophenoxy)-4-methoxy-benzaldehyde, prepared as described above in Example 5, in tetrahydrofuran (THF) (35 mL) was shaken in a Parr hydrogenator at 5 psi hydrogen with Raney nickel at 25° C. for 6 hours. The catalyst was filtered from the reaction and the solution evaporated in vacuo. The crude product was chromatographed, as described above in Example 2, through silica gel 60 using hexane:ethyl acetate (2:1), and recrystallized from ethanol (3A) to yield 1.79 g (60.1%) of product as white crystals.

Workup

  1. filtrationThe catalyst was filtered from the reaction
  2. customthe solution evaporated in vacuo
  3. customThe crude product was chromatographed
  4. customrecrystallized from ethanol (3A)

Sources & evidence

ORD record
ord-9a2d6efe3f1b491992ee3feb72e4c261
Source dataset
uspto-grants-1994_01
Patent number
US05281590

Reaction notes

Loading…