Triethylamine → 2-Methyl-4-[(2-nitrophenyl)amino]-2-butanol

HRID 1095394Notes

Reaction equation

HRID 1095394 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][CH2:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15].C(N(CC)CC)C>C1COCC1>[CH3:15][C:14]([OH:16])([CH2:13][CH2:12][NH:11][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 738951-Fluoro-2-nitrobenzeneHCID 156491734-Amino-2-methylbutan-2-ol

Product 1

HCID 574360482-Methyl-4-[(2-nitrophenyl)amino]-2-butanolYield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-fluoro-2-nitrobenzene (1.9 mL, 18 mmol), 4-amino-2-methyl-2-butanol (1.6 g, 15 mmol) and triethylamine (6.4 mL, 46 mmol) in THF (30 mL) was refluxed for 8 h. Then the reaction was quenched by addition of water (50 mL) and extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with brine (50 mL) and dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (5/1-2/1) to afford 2.8 g (82%) of the title compound.

Workup

  1. customThen the reaction was quenched by addition of water (50 mL)
  2. extractionextracted with ethyl acetate (50 mL×2)
  3. washThe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (5/1-2/1)

Sources & evidence

ORD record
ord-2cb60a186338465b983e51abcfa22dd8
Source dataset
uspto-grants-2012_03
Patent number
US08138177B2

Reaction notes

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