2-Methoxyaniline → HCID 1899153, compound

HRID 565179Notes

Reaction equation

HRID 565179 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH2:10]([O:12][CH2:13][CH2:14]Cl)[CH3:11].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:10]([O:12][CH2:13][CH2:14][NH:9][C:4]1[C:3](=[CH:8][CH:7]=[CH:6][CH:5]=1)[O:2][CH3:1])[CH3:11]

Participants

5

Reactant 3

HCID 70002-MethoxyanilineHCID 11430Potassium CarbonateHCID 12341Ethane, 1-chloro-2-ethoxy-

Product 1

HCID 1899153HCID 1899153, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 12.3 g (100 mmol) o-anisidine M10, 11.9 g (110 mmol) chloroethyl ethyl ether M14, 15.2 g (110 mmol) K2CO3 and 9.1 g (55 mmol) KI in 55 ml DMF was heated at 95° C. for 18 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 19.4 g crude oil. The crude oil was purified with a plug packed with 84 g silica gel 100 with CHCl3/cyclohexane (1:1, v/v) as eluant to afford 7.85 g pure product (yield: 40%).

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 19.4 g crude oil
  6. customThe crude oil was purified with a plug

Sources & evidence

ORD record
ord-1a836722ce334f47be49481475f866a8
Source dataset
uspto-grants-2001_01
Patent number
US06171866B2

Reaction notes

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