HCID 15229161, compound → HCID 15229162, compound

HRID 1646489Notes

Reaction equation

HRID 1646489 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-methoxybenzaldehyde, 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. Melting Point: 113°-115° C.

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-6cfea99a711f417c8c9deea615bbb059
Source dataset
uspto-grants-1993_01
Patent number
US05180720

Reaction notes

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