Hydrogen chloride-ethyl acetate → 3-methoxy-N-(4-methoxybutyl)-2-nitroaniline

HRID 1509463Notes

Reaction equation

HRID 1509463 reaction equation
C(OC(=O)[N:7]([CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH3:24])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[N+:16]([O-:18])=[O:17])(C)(C)C.C(OCC)(=O)C.Cl>C(OCC)(=O)C>[CH3:15][O:14][C:10]1[C:9]([N+:16]([O-:18])=[O:17])=[C:8]([CH:13]=[CH:12][CH:11]=1)[NH:7][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH3:24]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 58355557Tert-butyl (4-methoxybutyl)(3-methoxy-2-nitrophenyl)carbamate

Product 1

HCID 583557683-methoxy-N-(4-methoxybutyl)-2-nitroanilineYield 99.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl(4-methoxybutyl)(3-methoxy-2-nitrophenyl)carbamate (2.11 g) was dissolved in ethyl acetate (30 ml), 4M hydrogen chloride-ethyl acetate (15 ml) was added, and the mixture was stirred for 12 hr. The reaction mixture was concentrated under reduced pressure, diluted with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, concentration under reduced pressure to give the object product (1.50 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with saturated aqueous sodium hydrogen carbonate
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate, concentration under reduced pressure

Sources & evidence

ORD record
ord-bb37099e95634b35b72e3e3731f2d35d
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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