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

HRID 489646ノート

反応式

HRID 489646 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 135464462-(Pyridin-4-yl)aniline

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-11a10a81a4fd47138ff59eb4e2a4ee3e
出典データセット
uspto-grants-2005_12
特許番号
US06977264B2

反応ノート

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