HCID 19851963, compound → HCID 19851999, compound

HRID 1607147Notes

Reaction equation

HRID 1607147 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]([CH3:20])=[CH:17][C:18]=2[Br: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]([CH3:20])=[CH:17][C:18]=2[Br: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 19851963HCID 19851963, compound

Product 1

HCID 19851999HCID 19851999, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3.0 g of Raney nickel are added to a solution of 15.9 g (34.1 mmol) of 3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-4-bromo-6-methylnitrobenzene in 160 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]-4-bromo-6-methylaniline having a melting point of 108°-109° is obtained (ether/petroleum ether).

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-0d3da74fcd004e498965af04bfe82ee8
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

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