HCID 19851988, compound → HCID 19851936, compound

HRID 1607155Notes

Reaction equation

HRID 1607155 reaction equation
[C:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([N+:21]([O-])=O)[C:16]([Cl:20])=[CH:17][C:18]=2[CH3:19])=[C:6]([CH2:26][CH2:27][CH3:28])[C:5]=1[OH:29])(=[O:3])[CH3:2]>[Ni].O1CCCC1>[C:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([C:16]([Cl:20])=[CH:17][C:18]=2[CH3:19])[NH2:21])=[C:6]([CH2:26][CH2:27][CH3:28])[C:5]=1[OH:29])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 19851988HCID 19851988, compound

Product 1

HCID 19851936HCID 19851936, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4.0 g of Raney nickel are added to a solution of 19 g (45 mmol) of 3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-4-methyl-6-chloronitrobenzene in 200 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 and the residue is recrystallised from ether/hexane. 3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-4-methyl-6-chloroaniline having a melting point of 81° C. is obtained.

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
  5. customthe residue is recrystallised from ether/hexane

Sources & evidence

ORD record
ord-ca6133b8617747579130548798683c2c
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

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