2-Methoxyaniline → 2-Methoxycyclohexan-1-amine

HRID 736994Notes

Reaction equation

HRID 736994 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1>CC(O)=O.[Rh]>[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[NH2:9]

Participants

4

Reactant 1

HCID 70002-Methoxyaniline

Product 1

HCID 222508792-Methoxycyclohexan-1-amineYield 22.7%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolvent

Procedure

Shake a mixture of o-anisidine (5.0 g, 41 mmol) and rhodium on carbon (5% Rh; 5.0 g) in AcOH (65 mL) under H2 (60 psig) at 60° C. for 6 h. Filter the reaction mixture and rotary, evaporate the filtrate (75° C.). Dissolve this material in CHCl3 (100 mL) and basifiy with satd aq NaHCO3 (50 mL). Dry the organic layer (Na2SO4) and rotary evaporate (40° C.) to yield 1.20 g of 2-methoxy-cyclohexylamine as a yellow oil.

Workup

  1. filtrationFilter the reaction mixture
  2. customrotary, evaporate the filtrate (75° C.)
  3. dissolutionDissolve this material in CHCl3 (100 mL)
  4. dry with materialDry the organic layer (Na2SO4)
  5. customrotary evaporate (40° C.)

Sources & evidence

ORD record
ord-af94ccf13549479995208b87366a228e
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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