HCID 13799289, compound → HCID 13799292, compound

HRID 652318Notes

Reaction equation

HRID 652318 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[Cl:19])=[C:6]([CH2:26][CH2:27][C:28]([F:31])([F:30])[F:29])[C:5]=1[OH:32])(=[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[Cl:19])[NH2:21])=[C:6]([CH2:26][CH2:27][C:28]([F:29])([F:30])[F:31])[C:5]=1[OH:32])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 13799289HCID 13799289, compound

Product 1

HCID 13799292HCID 13799292, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.0 g of Raney nickel is added to a solution of 3.7 g of 3-[3-(4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy)-propoxy]-4-chloro-6-methyl-nitrobenzene in 40 ml of tetrahydrofuran and the starting substance is hydrogenated at room temperature. The catalyst is filtered off and washed with tetrahydrofuran. The filtrate is evaporated to dryness under reduced pressure and the residue is crystallised from ether/petroleum ether. 3-{3-[4-Acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-4-chloro-6-methyl-aniline of melting point 111°-113° is thus obtained.

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe catalyst is filtered off
  3. washwashed with tetrahydrofuran
  4. customThe filtrate is evaporated to dryness under reduced pressure
  5. customthe residue is crystallised from ether/petroleum ether

Sources & evidence

ORD record
ord-440514cef65841afad6f23a8efc506ae
Source dataset
uspto-grants-1987_06
Patent number
US04670604

Reaction notes

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