Water → tert-butyl N-[(4-aminophenyl)methyl]carbamate

HRID 2106172Notes

Reaction equation

HRID 2106172 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+].O>[Fe].C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 10610803tert-Butyl 4-nitrobenzylcarbamate

Product 1

HCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateYield 90%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 1140TolueneSolvent

Procedure

(4-Nitro-benzyl)-carbamic acid tert-butyl ester (6.34 g, 25.1 mmol), iron powder (6.5 g, 116 mmol), ammonium formate (13.0 g, 206 mmol), H2O (75 mls), and toluene (75 mls) were combined and heated to reflux. After 3 hrs the reaction mixture was allowed to cool and filtered through Celite with thorough washing with EtOAc. The filtrate was transferred to a separatory funnel and the phases separated. The organic phase was further washed with H2O (1×), sat'd NaCl (1×), dried (Na2SO4), and concentrated in vacuo to give (4-amino-benzyl)-carbamic acid tert-butyl ester (5.02 g, 90% yield). LC/MS Calcd for [M+H]+ 223.1, found 167.1 (minus t-butyl).

Workup

  1. temperatureheated to reflux
  2. temperatureto cool
  3. filtrationfiltered through Celite
  4. washwith thorough washing with EtOAc
  5. customThe filtrate was transferred to a separatory funnel
  6. customthe phases separated
  7. washThe organic phase was further washed with H2O (1×), sat'd NaCl (1×)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b030ac70f5ff41338135e0e6f9f99bf4
Source dataset
uspto-grants-2009_08
Patent number
US07579473B2

Reaction notes

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