2-Methoxyethanol → 4-Cyano-3-(2-methoxyethoxy)aniline

HRID 393582Notes

Reaction equation

HRID 393582 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][OH:7].[NH2:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11](Cl)[CH:10]=1>CN1C(=O)CCC1.O>[C:13]([C:12]1[CH:15]=[CH:16][C:9]([NH2:8])=[CH:10][C:11]=1[O:7][CH2:6][CH2:5][O:4][CH3:3])#[N:14]

Participants

6

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 887284-Amino-2-chlorobenzonitrile

Product 1

HCID 226465404-Cyano-3-(2-methoxyethoxy)anilineYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

Sodium hydride (300 mg of an 80% suspension in mineral oil, 10 mmol) was added to 2-methoxyethanol (0.76 g, 10 mmol) in NMP (5 ml) and the mixture stirred for 15 minutes. 4-Amino-2-chlorobenzonitrile (1.5 g, 10 mmol) was added and the mixture heated at 100° C. for 5 hours. The mixture was allowed to cool, diluted with water and extracted with ethyl acetate (3×50 ml). The combined extracts were dried (MgSO4) and the solvent removed by evaporation. The residue was purified by chromatography eluting with increasingly polar mixtures of methylene chloride/ethyl acetate to give 4-cyano-3-(2-methoxyethoxy)aniline (760 mg, 40%) as a dark yellow oil.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customthe solvent removed by evaporation
  5. customThe residue was purified by chromatography
  6. washeluting
  7. temperaturewith increasingly polar mixtures of methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-9e8d38ce1e9944648bfcdeff6518031c
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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