Ammonium Chloride → Tert-butyl 3-amino-4-chlorobenzylcarbamate

HRID 1258624Notes

Reaction equation

HRID 1258624 reaction equation
[NH4+].[Cl-].[Cl:3][C:4]1[CH:18]=[CH:17][C:7]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][C:5]=1[N+:19]([O-])=O>[Fe].CCO>[NH2:19][C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][C:4]=1[Cl:3])[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 22981312tert-Butyl 4-chloro-3-nitrobenzylcarbamate

Product 1

HCID 22981266Tert-butyl 3-amino-4-chlorobenzylcarbamate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Sat. aq. NH4Cl (50 mL) followed by iron powder (5.51 g, 98.7 mmol) were added at rt to a mixture of tert-butyl 4-chloro-3-nitrobenzylcarbamate (5.66 g, 19.7 mmol) and EtOH (50 mL). After stirring for 4 h at 80° C., 4 h at 90° C. and at rt overnight the reaction mixture was filtered through celite and washed with EtOAc. The aq. layer was extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and concentrated to give the sub-title compound.

Workup

  1. filtrationwas filtered through celite
  2. washwashed with EtOAc
  3. extractionThe aq. layer was extracted with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cdd280aac7974714b5bfef5d93b39512
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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