HCID 86735506, compound → HCID 86735505, compound

HRID 616869Notes

Reaction equation

HRID 616869 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:17])([F:16])[F:15])[CH:5]=[C:4]([N+:18]([O-])=O)[C:3]=1[O:21][C:22]1[C:27]([N+:28]([O-])=O)=[CH:26][C:25]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]([F:40])([F:39])[F:38])=[CH:24][C:23]=1[Cl:41].[H][H]>C(O)C.O=[Pt]=O>[NH2:18][C:4]1[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:16])([F:17])[F:15])[CH:7]=[C:2]([Cl:1])[C:3]=1[O:21][C:22]1[C:23]([Cl:41])=[CH:24][C:25]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]([F:40])([F:39])[F:38])=[CH:26][C:27]=1[NH2:28]

Participants

5

Reactant 2

HCID 86735506HCID 86735506, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86735505HCID 86735505, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-chloro-α,α,α-trifluoro-6-nitro-p-tolylphenyl ether (150 g., 0.472 mole) in ethanol (1200 ml.) was shaken in an atmosphere of hydrogen in a Parr apparatus in the presence of PtO2 (600 mg.) until uptake ceased. The catalyst was filtered off, the solvent removed, and the residue taken up in pentane (600 ml.) and filtered through activated silica gel (~ 15 g.) and the solvent removed. The residue was recrystallized from pentane at -20° C. to give 2-amino-6-chloro-α,α,α-trifluoro-p-tolylphenyl ether (94.1 g., 70%) m.p. 47-53° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed
  3. filtrationfiltered through activated silica gel (~ 15 g.)
  4. customthe solvent removed
  5. customThe residue was recrystallized from pentane at -20° C.

Sources & evidence

ORD record
ord-d337069b28c4469c8aba6090fa689a7d
Source dataset
uspto-grants-1978_02
Patent number
US04076741

Reaction notes

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