2-Chloro-N,N-dimethylethylamine → 1-(2-Dimethylaminoethoxy)-3-nitrobenzene

HRID 1740791Notes

Reaction equation

HRID 1740791 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16]Cl>CN(C)C=O>[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 111373-NitrophenolHCID 24758Sodium hydride

Product 1

HCID 218331171-(2-Dimethylaminoethoxy)-3-nitrobenzeneYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred soluton of 3-nitrophenol (5 g, 36 mmol) in dimethylformamide (100 ml) at 0° C. was added sodium hydride (1.029 g, 80% dispersion in mineral oil, 34.3 mmol). After the effervescence had subsided 2-dimethylaminoethyl chloride was added (5.746 g, 37.8 mmol). After 1 hour the reaction mixture was allowed to warm to room temperature. After a further 2 hours the reaction mixture was heated to 70° C. for 14 hours, then evaporated under reduced pressure. The residue was then partitioned between water and ethyl acetate and the organic phase washed twice with aqueous sodium hydroxide solution (SM) and then saturated aqueous sodium chloride solution. Drying and evaporation gave the product as a brown oil (4.64 g, 61%)

Workup

  1. additionwas added (5.746 g, 37.8 mmol)
  2. temperatureAfter a further 2 hours the reaction mixture was heated to 70° C. for 14 hours
  3. customevaporated under reduced pressure
  4. customThe residue was then partitioned between water and ethyl acetate
  5. washthe organic phase washed twice with aqueous sodium hydroxide solution (SM)
  6. customDrying
  7. customevaporation

Sources & evidence

ORD record
ord-79e8af7ec33f43c28b9464987acf6aec
Source dataset
uspto-grants-1999_10
Patent number
US05972937

Reaction notes

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