4,5-Dihydro-2-[2-(2-methoxy-5-nitrophenyl)ethenyl]-4,4-dimethyloxazole → 3-[2-(4,5-Dihydro-4,4-dimethyl-2-oxazolyl)ethyl]-4-methoxybenzenamine

HRID 621465Notes

Reaction equation

HRID 621465 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[CH:12]=[CH:13][C:14]1[O:15][CH2:16][C:17]([CH3:20])([CH3:19])[N:18]=1.[H][H]>[Ni].CO>[CH3:19][C:17]1([CH3:20])[CH2:16][O:15][C:14]([CH2:13][CH2:12][C:4]2[CH:5]=[C:6]([NH2:9])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[N:18]1

Participants

5

Reactant 2

HCID 538942974,5-Dihydro-2-[2-(2-methoxy-5-nitrophenyl)ethenyl]-4,4-dimethyloxazoleHCID 178418361HCID 178418361, compound2×

Product 1

HCID 144076263-[2-(4,5-Dihydro-4,4-dimethyl-2-oxazolyl)ethyl]-4-methoxybenzenamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney nickel, 3 g, is added to a solution of 4,5-dihydro-2-[2-(2-methoxy-5-nitrophenyl)ethenyl]-4,4-dimethyloxazole, 10.9 g, in methanol, 500 ml. The mixture is exposed to hydrogen gas until the appropriate quantity of hydrogen is taken up, filtered and the solvent evaporated to give 10.2 g of 3-[2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)ethyl]-4-methoxybenzenamine as a gum. To an ice cold solution of the previous crude gum and 7 ml of triethylamine in chloroform is added 10.5 g of 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoyl chloride (U.S. Pat. No. 4,285,951). The mixture is worked up, chromatographed over silica gel and eluted with diethylether to give 10.5 g of N-[3-[2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)ethyl]-4-methoxyphenyl]-5-(2,5-dimethylphenoxy)-2,2-dimethylpentanamide as a gum; thin layer chromatography on silica gel: Rf =0.57 (ethyl acetate).

Workup

  1. filtrationfiltered
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-fd0a722e9512461ba802021fb3693307
Source dataset
uspto-grants-1989_04
Patent number
US04824843

Reaction notes

Loading…