HCID 19818654, compound → HCID 19852012, compound

HRID 1607144Notes

Reaction equation

HRID 1607144 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([N+:20]([O-])=O)[C:16]([CH3:19])=[CH:17][CH:18]=2)=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2]>[Ni].O1CCCC1>[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([C:16]([CH3:19])=[CH:17][CH:18]=2)[NH2:20])=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 19818654HCID 19818654, compound

Product 1

HCID 19852012HCID 19852012, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.0 g of Raney nickel is added to a solution of 9.1 g (23.5 mmol) of 3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-6-methylnitrobenzene in 90 ml of tetrahydrofuran and the whole is hydrogenated at room temperature. The catalyst is filtered off and washed with tetrahydrofuran. The filtrate is concentrated to dryness by evaporation under reduced pressure. 3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-6-methylaniline is obtained having an Rf value=0.12 (silica gel/methylene chloride).

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe catalyst is filtered off
  3. washwashed with tetrahydrofuran
  4. concentrationThe filtrate is concentrated to dryness by evaporation under reduced pressure

Sources & evidence

ORD record
ord-4153ac618f824e519365bb3d918c71b6
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

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