2-Chloro-4-fluoro-6-nitrophenol → 2-Chloro-4-fluoro-6-aminophenol Hydrochloride

HRID 1456655Notes

Reaction equation

HRID 1456655 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[OH:12].[H][H]>CCO.[Pt]=O>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([NH2:9])[C:3]=1[OH:12]

Participants

5

Reactant 2

HCID 37278862-Chloro-4-fluoro-6-nitrophenolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 221171192-Chloro-4-fluoro-6-aminophenol HydrochlorideYield 141.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of compound 711 (23.4 g, 0.122 mol) and platinum oxide (2.3 g) in absolute EtOH (120 mL) was placed under 1 atm of hydrogen and stirred until complete reduction had occurred. The hydrogen was replaced with nitrogen and the reaction was filtered through Celite. The filtrate was diluted with Et2O (300 mL) and gaseous hydrochloric acid was bubbled through the solution to provide a white precipitate. The solid was collected and dried under vacuum to provide 17.1 g of compound 712 as a white solid. ##STR91##

Workup

  1. filtrationthe reaction was filtered through Celite
  2. additionThe filtrate was diluted with Et2O (300 mL) and gaseous hydrochloric acid
  3. customwas bubbled through the solution
  4. customto provide a white precipitate
  5. customThe solid was collected
  6. customdried under vacuum

Sources & evidence

ORD record
ord-2dcc895c2f8f4a83b59979bb34231267
Source dataset
uspto-grants-1998_12
Patent number
US05843904

Reaction notes

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