Ethanol → (5-Amino-2-cyanobenzyl)carbamic acid t-butyl ester

HRID 1157946Notes

Reaction equation

HRID 1157946 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[C:18]#[N:19])([CH3:4])([CH3:3])[CH3:2].C(O)C.[Cl-].[NH4+]>[Fe].O>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[C:18]#[N:19])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 59511869(2-Cyano-5-nitrobenzyl)carbamic Acid t-Butyl Ester

Product 1

HCID 59511863(5-Amino-2-cyanobenzyl)carbamic acid t-butyl esterYield 92.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a mixture of (2-cyano-5-nitrobenzyl)carbamic acid t-butyl ester (2.39 g) and ethanol (180 mL) there were added water (12 mL), saturated aqueous ammonium chloride (5 mL) and iron powder (2.02 g), under a nitrogen atmosphere. The mixture was heated to reflux for 2 hours and then filtered through Celite to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure to obtain a residue. The Celite and filtered substance were washed with ethyl acetate (400 mL) and water (200 mL) in that order, and this washed solution was combined with the previous residue. After sufficiently shaking the mixture, the organic layer was separated off and the organic layer was dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture) to obtain the target compound (1.97 g) as an off-white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationfiltered through Celite
  4. customto obtain a filtrate
  5. distillationthe solvent in the filtrate was distilled off under reduced pressure
  6. customto obtain a residue
  7. filtrationThe Celite and filtered substance
  8. washwere washed with ethyl acetate (400 mL) and water (200 mL) in that order
  9. customthe organic layer was separated off
  10. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  11. filtrationThe mixture was filtered
  12. customto obtain a filtrate
  13. distillationthe solvent in the filtrate was distilled off under reduced pressure
  14. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture)

Sources & evidence

ORD record
ord-4253e8dc352f45b9beffdb42757d7104
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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