HCID 21129879, compound → HCID 21129881, compound

HRID 1675187Notes

Reaction equation

HRID 1675187 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[C:15]([Cl:22])[C:3]=1[O:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2>ClC1C=C([N+]([O-])=O)C=C(Cl)C=1OC1C=NC2C(C=1)=CC=CC=2.C(OCC)(=O)C.[Pt]>[Cl:1][C:2]1[CH:18]=[C:17]([NH2:19])[CH:16]=[C:15]([Cl:22])[C:3]=1[O:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

5

Reactant 1

HCID 21129879HCID 21129879, compound

Product 1

HCID 21129881HCID 21129881, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 21129879HCID 21129879, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

The nitro functionality of 3-(2,6-dichloro-4-nitro-phenoxy)-quinoline (4) was catalytically reduced under hydrogen with 5% weight/weight (catalyst/compound 4) of a 1% platinum/2% vanadium on carbon catalyst suspension in ethyl acetate at 0° C. The material was heated to 20° C., filtered through Celite. The Celite was washed with THF, and the filtrates were combined and evaporated to give 3,5-dichloro-4-(quinolin-3-yloxy)-phenylamine (5) in 98% yield.

Workup

  1. filtrationfiltered through Celite
  2. washThe Celite was washed with THF
  3. customevaporated

Sources & evidence

ORD record
ord-859564f1fc0f47eebd0d8e9ba3f49177
Source dataset
uspto-grants-2011_08
Patent number
US08003665B2

Reaction notes

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