Acetic Acid → 1-(4-Amino-2-fluoro-phenyl)-2,3-dihydro-1H-pyridin-4-one

HRID 896174

反応式

HRID 896174 の反応式
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH:16]=[CH:15][C:14](=[O:17])[CH2:13][CH2:12]1.C(O)(=O)C.[H][H]>C1COCC1.[Pd].C([O-])([O-])=O.[Ca+2]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH:12]=[CH:13][C:14](=[O:17])[CH2:15][CH2:16]2)=[C:2]([F:1])[CH:7]=1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 218776411-(2-fluoro-4-nitrophenyl)-2,3-dihydro-1H-pyridin-4-oneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 218778771-(4-Amino-2-fluoro-phenyl)-2,3-dihydro-1H-pyridin-4-one

試薬・触媒・溶媒 2

HCID 12000666Calcium Palladium Carbonate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

In a 500 ml Parr bottle, 1-(2-fluoro-4-nitrophenyl)-2,3-dihydro-1H-pyridin-4-one (Step 3, 35 g, 148.3 mmol), Pd/CaCO3 (3.5 g, 10 wt %) and acetic acid (17 ml, 297 mmol) are combined in THF (350 ml). The mixture is hydrogenated at 40° C. under 15 psi hydrogen for 6 h at which time the reaction is complete by HPLC. The reaction mixture is filtered through a GF/F filter and the catalyst cake washed with THF (350 ml). The filtrate is partitioned between 500 ml of NaHCO3 and 500 ml of ethyl acetate. The organic layer is washed again with 500 ml of NaHCO3. The organic layer is separated and dried over MgSO4. The mixture is filtered, and the filtrate is concentrated under reduced pressure to afford 29.0 g (95% recovery) of the title compound, MS (ESI−) for C11H11FN2O m/z 205.0 (M−H)−; 1H NMR (MeOD) δ 7.37 (d, 1 H), 7.02 (t, 1 H), 6.47 (m, 3 H), 5.07 (d, 1 H), 3.84 (t, 2 H), 2.58 (t, 1H).

後処理

  1. filtrationThe reaction mixture is filtered through a GF/F
  2. filtrationfilter
  3. washthe catalyst cake washed with THF (350 ml)
  4. customThe filtrate is partitioned between 500 ml of NaHCO3 and 500 ml of ethyl acetate
  5. washThe organic layer is washed again with 500 ml of NaHCO3
  6. customThe organic layer is separated
  7. dry with materialdried over MgSO4
  8. filtrationThe mixture is filtered
  9. concentrationthe filtrate is concentrated under reduced pressure

出典と根拠

ORDレコード
ord-578df401533f4574922dc620475f9d60
出典データセット
uspto-grants-2005_07
特許番号
US06919329B2

関連ノート

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