1-(3-Fluorobenzyloxy)-2-methyl-4-nitrobenzene → 3-Methyl-4-[(3-fluorobenzyl)oxy]aniline

HRID 550413Notes

Reaction equation

HRID 550413 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[CH3:16].[H][H]>C(O)C.O=[Pt]=O>[CH3:16][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:7]=1[O:6][CH2:5][C:4]1[CH:17]=[CH:18][CH:19]=[C:2]([F:1])[CH:3]=1)[NH2:13]

Participants

5

Reactant 2

HCID 221379601-(3-Fluorobenzyloxy)-2-methyl-4-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 221379333-Methyl-4-[(3-fluorobenzyl)oxy]anilineYield 100.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-[(3-fluorobenzyl)oxy]-2-methyl-4-nitrobenzene (3.2 g, 12.2 mmol) and PtO2 (320 mg) in ethanol (250 ml) was stirred under an atmosphere of hydrogen (1.2 bar) until completion of the reaction (the reaction being complete when 3 mole equivalents of hydrogen have been reacted). The mixture was then filtered over celite and the solvent evaporated to give 3-methyl-4-[(3-fluorobenzyl)oxy]aniline as a yellow oil (2.83 g, 100%);

Workup

  1. customhave been reacted)
  2. filtrationThe mixture was then filtered over celite
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-9efa0effb77745d5a0f2f7e81f956d62
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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