2-Methoxyaniline → HCID 21267687, compound

HRID 565181Notes

Reaction equation

HRID 565181 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][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.C(Cl)(Cl)Cl>[O:13]([CH2:12][CH2:11][NH:9][C:4]1[C:3](=[CH:8][CH:7]=[CH:6][CH:5]=1)[O:2][CH3:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 70002-MethoxyanilineHCID 11430Potassium CarbonateHCID 68526Benzene, (2-bromoethoxy)-

Product 1

HCID 21267687HCID 21267687, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of 6.2 g (50 mmol) o-anisidine M10, 12.1 g (60 mmol) β-bromophenetole M20 and 8.3 g (60 mmol) K2CO3 in 25 ml acetonitrile was heated at reflux for 18 hours. The mixture was cooled, diluted with 100 ml CHCl3 and washed with 100 ml water and 100 ml saturated NaCl. The organic layer was dried over Na2SO4. The solvent was evaporated to give 14.5 g crude oil. This oil was purified by a plug packed with 60 g silica gel 100 with cyclohexane as eluant, wherein 6.4 g pure product were obtained (yield: 51%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. washwashed with 100 ml water and 100 ml saturated NaCl
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customThe solvent was evaporated
  7. customto give 14.5 g crude oil
  8. customThis oil was purified by a plug

Sources & evidence

ORD record
ord-3bf0d287962b4682a5146c47a521ea54
Source dataset
uspto-grants-2001_01
Patent number
US06171866B2

Reaction notes

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