Ethanolamine → HCID 68325669, compound

HRID 571836Notes

Reaction equation

HRID 571836 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]2[CH2:13][O:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[NH2:14][CH2:15][CH2:16][OH:17].CCOC(C)=O.C1COCC1>C1COCC1>[OH:17][CH2:16][CH2:15][NH:14][CH2:13][CH:11]([C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=1)[OH:12]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 21939870Tetrahydrofuran ethyl acetateHCID 86671392HCID 86671392, compound

Product 1

HCID 68325669HCID 68325669, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (RS)-2-(3-methyl-4-nitrophenyl)oxirane (4.63 g) in THF (15 ml) was added 2-aminoethanol (15.5 ml) and the mixture was stirred at room temperature overnight. The reaction mixture was then poured into EtOAc/THF (1:1) and extracted with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford (RS)-2-(2-hydroxyethylamino)-1-(3-methyl-4-nitrophenyl)ethanol (6.84 g, quant.) as a brown oil which was used in the next step without further purification. MS (ISP): 241.1 ([M+H]+).

Workup

  1. extractionextracted with saturated brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a041dc63ac645db925a4889088c73e4
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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