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

HRID 886992Notes

Reaction equation

HRID 886992 reaction equation
[N+:1]([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][CH:5]=1)([O-])=O.C(O)C.O.[Cl-].[NH4+]>O1CCOCC1>[NH2:1][C:4]1[CH:18]=[CH:17][C:7]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 10610803tert-Butyl 4-nitrobenzylcarbamate

Product 1

HCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

C4 (7.0 g, 27.7 mmol) was dissolved in dioxane (325 mL), ethanol (240 mL), and water (160 mL). The resultant solution was then treated with Fe(0) powder (7.12 g, 127.4 mmol) and ammonium chloride (5.33 g, 99.7 mmol), and the resultant mixture was stirred at 70° C. for 4 hours. The reaction mixture was cooled to 25° C., filtered through Celite®, and washed with EtOAc. The organic solvents were evaporated, and the resultant aqueous residue was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated to provide C5 as a yellow solid. Yield: 6.52 g, 99% yield. 1H NMR (400 MHz, d6-DMSO) δ: 7.146 (t, 1H), 6.87 (d, 2H), 6.48 (d, 2H), 4.95 (s, 2H), 3.92 (d, 2H), 1.38 (s, 9H).

Workup

  1. filtrationfiltered through Celite®
  2. washwashed with EtOAc
  3. customThe organic solvents were evaporated
  4. extractionthe resultant aqueous residue was extracted with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-320484cffa0046e9a12366013b856f1e
Source dataset
uspto-grants-2012_08
Patent number
US08247411B2

Reaction notes

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