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

HRID 2077064Notes

Reaction equation

HRID 2077064 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-e3f97a5da47f480180e348a4dd9ebe30
Source dataset
uspto-grants-2011_04
Patent number
US07928109B2

Reaction notes

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