N-(2-tert-butyl-5-nitrophenyl)-2-(dimethylamino)acetamide → Ammonium Hydroxide

HRID 2211645Notes

Reaction equation

HRID 2211645 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=[O:12])=[CH:7][C:6]=1[NH:14][C:15](=[O:20])[CH2:16][N:17]([CH3:19])[CH3:18])([CH3:4])([CH3:3])[CH3:2]>CCO.O1CCOCC1>[NH4+:11].[OH-:12].[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[C:6]([NH:14][C:15](=[O:20])[CH2:16][N:17]([CH3:18])[CH3:19])[CH:7]=1

Participants

5

Reactant 1

HCID 21961377N-(2-tert-butyl-5-nitrophenyl)-2-(dimethylamino)acetamide

Product 2

HCID 14923Ammonium HydroxideHCID 21961467HCID 21961467, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(2-tert-Butyl-5-nitro-phenyl)-2-dimethylamino-acetamide (25.8 g, 92 mmol) was dissolved in EtOH (1.4 L) and 1,4-dioxane (200 mL). The solution was degassed under vacuum with stirring. 10% Pd/C (2.5 g) was added (as a slurry in EtOH). The mixture was degassed again, then the reaction vessel was charged with H2 gas (balloon) and stirred overnight at RT. The reaction was filtered through Celite® with MeOH and the filtrate was concentrated under reduced pressure. The recovered material was eluted through a 36×7 cm column of silica gel with a 97.5:2.5:0.25 and 95:5:0.5 CH2Cl2:MeOH:NH4OH(aq) step gradient giving N-(5-amino-2-tert-butyl-phenyl)-2-dimethylamino-acetamide as a brown solid.

Workup

  1. customThe solution was degassed under vacuum
  2. addition10% Pd/C (2.5 g) was added (as a slurry in EtOH)
  3. customThe mixture was degassed again
  4. additionthe reaction vessel was charged with H2 gas (balloon)
  5. stirringstirred overnight at RT
  6. filtrationThe reaction was filtered through Celite® with MeOH
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washThe recovered material was eluted through a 36×7 cm column of silica gel with a 97.5:2.5:0.25 and 95:5:0.5 CH2Cl2

Sources & evidence

ORD record
ord-fc22478adad04de9b8cd23c38215d7ba
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

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