HCID 59410042, compound → HCID 59410052, compound

HRID 2404873Notes

Reaction equation

HRID 2404873 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 59410042HCID 59410042, compound

Product 1

HCID 59410052HCID 59410052, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask charged with 1-(2-tert-butyl-5-nitrophenyl)pyrrolidine (150 mg, 0.60 mmol) and Pd/C (15 mg, 0.14 mmol) was flushed under N2 followed by evacuating under vacuum. Methanol (2 mL) was added under inert atmosphere followed by evacuating under vacuum. The reaction mixture was stirred overnight under an atmosphere of H2. The reaction mixture was filtered and the solvent was evaporated to give 4-tert-butyl-3-(pyrrolidin-1-yl)aniline (119 mg, 90%). LC/MS: m/z 218.5 (M+H)+ at 2 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customwas flushed under N2
  2. customby evacuating under vacuum
  3. additionMethanol (2 mL) was added under inert atmosphere
  4. customby evacuating under vacuum
  5. filtrationThe reaction mixture was filtered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-90b996c3ff2f42b79636faf50d86ec74
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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