diethyl 3,4-dihydro-7-[3-(4-nitrophenoxy)propoxy]-4-oxo-8-propyl-2H-1-benzopyran-2,2-dipropanoate → diethyl 7-[3-(4-aminophenoxy)propoxy]-3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-2,2-dipropanoate

HRID 2371631Notes

Reaction equation

HRID 2371631 reaction equation
[N+:1]([C:4]1[CH:42]=[CH:41][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:37]=[CH:36][C:16]3[C:17](=[O:35])[CH2:18][C:19]([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:20][C:15]=3[C:14]=2[CH2:38][CH2:39][CH3:40])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:37]=[CH:36][C:16]3[C:17](=[O:35])[CH2:18][C:19]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[O:20][C:15]=3[C:14]=2[CH2:38][CH2:39][CH3:40])=[CH:41][CH:42]=1

Participants

4

Reactant 1

HCID 15157455diethyl 3,4-dihydro-7-[3-(4-nitrophenoxy)propoxy]-4-oxo-8-propyl-2H-1-benzopyran-2,2-dipropanoate

Product 1

HCID 15157464diethyl 7-[3-(4-aminophenoxy)propoxy]-3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-2,2-dipropanoate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 363 mg (0.62 mmol) of the title product of Example 38 in 45 ml of ethanol was treated with 36 mg of Raney nickel and then hydrogenated at atmospheric pressure and room temperature for 3.25 hr. The reaction mixture was filtered and the solvent was removed under reduced pressure. Chromotography of the residue over silica gel using 50-50 ethyl acetate/hexane as eluent gave the title compound as a white solid, m.p. 125.5°-127° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a526a254bcbc4616bf7a8f55bcb9e68f
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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