Hydrochloric Acid → 2-(Pyridin-4-yl)aniline

HRID 489646Notes

Reaction equation

HRID 489646 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)([O-])=O.Cl>CO>[N:13]1[CH:14]=[CH:15][C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH2:1])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 110198764-(2-Nitrophenyl)pyridine

Product 1

HCID 135464462-(Pyridin-4-yl)aniline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a 500 mL round-bottomed flask was added a solution of 4-(2-nitrophenyl)-pyridine (Step a) (7.1 g, 36 mmol) in MeOH (300 mL). The solution was treated dropwise with concd HCl (6.7 mL, 84 mmol) and purged with N2. Pd/C (10%, Aldrich) (2.5 g) was added, H2 was introduced and the suspension was magnetically stirred under atmospheric H2 pressure for 15 h at 25° C. The suspension was purged with N2, filtered through Celite® (Aldrich) (25 g) and the filter cake was washed with MeOH (400 mL). The filtrate was concentrated in vacuo to a yellow powder which was partitioned between EtOAc (200 mL) and 1 N NaOH (100 mL). The organic layer was washed with water (100 mL), satd NaCl (50 mL), dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound as a viscous yellow oil which solidified upon standing (6.0 g). MP 81-83° C. MS (ESI, pos. ion) m/z: 171 (M+1); (ESI, neg. ion) m/z: 169 (M−1). Calc'd for C11H10N2: 170.21.

Workup

  1. custompurged with N2
  2. additionPd/C (10%, Aldrich) (2.5 g) was added
  3. additionH2 was introduced
  4. customThe suspension was purged with N2
  5. filtrationfiltered through Celite® (Aldrich) (25 g)
  6. washthe filter cake was washed with MeOH (400 mL)
  7. concentrationThe filtrate was concentrated in vacuo to a yellow powder which
  8. customwas partitioned between EtOAc (200 mL) and 1 N NaOH (100 mL)
  9. washThe organic layer was washed with water (100 mL), satd NaCl (50 mL)
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11a10a81a4fd47138ff59eb4e2a4ee3e
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

Loading…