2-Methoxyaniline → Benzenamine, N-butyl-2-methoxy-

HRID 565180Notes

Reaction equation

HRID 565180 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.Br[CH2:11][CH2:12][CH2:13][CH3:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:11]([NH:9][C:4]1[C:3](=[CH:8][CH:7]=[CH:6][CH:5]=1)[O:2][CH3:1])[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 70002-MethoxyanilineHCID 8002Butyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 103412Benzenamine, N-butyl-2-methoxy-Yield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6.2 g (50 mmol) o-anisidine M10, 7.5 g (55 mmiol) 1-bromobutane M17, 7.6 g (55 mmol) K2CO3 and 0.91 g (5.5 mmol) KI in 25 ml DMF was heated at 95° C. for 24 hours. DMF was evaporated and the residue was dissolved in 100 ml CHCl3 and 100 ml saturated NaCl. The organic layer was dried over Na2SO4. The solvent was evaporated to give 9.4 g crude oil. This oil was purified by a plug packed with 45 g silica gel 100 using cyclohexane as eluant, wherein 4.8 g pure product were obtained (yield: 55%).

Workup

  1. customDMF was evaporated
  2. dissolutionthe residue was dissolved in 100 ml CHCl3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customThe solvent was evaporated
  5. customto give 9.4 g crude oil
  6. customThis oil was purified by a plug

Sources & evidence

ORD record
ord-f17eacdab28743e1b6bc77e64a52ec9f
Source dataset
uspto-grants-2001_01
Patent number
US06171866B2

Reaction notes

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