3-Fluoro-2-trifluoromethyl-pyridine-4-carbaldehyde oxime → 4-Pyridinemethanamine, 3-fluoro-2-(trifluoromethyl)-

HRID 1527469ノート

反応式

HRID 1527469 の反応式
[F:1][C:2]1[C:3]([C:11]([F:14])([F:13])[F:12])=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[N:9]O>C(O)(=O)C.[Zn]>[F:1][C:2]1[C:3]([C:11]([F:13])([F:14])[F:12])=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][NH2:9]

参加物

4

反応物 1

HCID 1363523253-Fluoro-2-trifluoromethyl-pyridine-4-carbaldehyde oxime

生成物 1

HCID 682841474-Pyridinemethanamine, 3-fluoro-2-(trifluoromethyl)-

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

Zinc dust (0.63 g, 9.62 mmol) was added at RT to a solution of 3-fluoro-2-trifluoromethyl-pyridine-4-carbaldehyde oxime (0.460 g, 1.57 mmol) in acetic acid (8 mL). The reaction mixture was stirred at RT for 3 h, then filtered through a 0.45 microns filter, and the filtrate was concentrated in vacuo. The colored oily residue was partitioned between CH2Cl2 and 1N HCl, the layers were separated and the aqueous phase was extracted twice with CH2Cl2. The pH of the aqueous layer was then adjusted to pH=9 by adding a saturated aqueous NaHCO3 solution, and the resulting white suspension was extracted four times with CH2Cl2. The combined organics were dried (phase separator) and concentrated in vacuo to afford the title compound as a yellow oil. MS (LC/MS): 195.0 [M+H]+; tR (HPLC conditions c): 2.47 min.

後処理

  1. filtrationfiltered through a 0.45 microns
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe colored oily residue was partitioned between CH2Cl2 and 1N HCl
  5. customthe layers were separated
  6. extractionthe aqueous phase was extracted twice with CH2Cl2
  7. additionby adding a saturated aqueous NaHCO3 solution
  8. extractionthe resulting white suspension was extracted four times with CH2Cl2
  9. customThe combined organics were dried (phase separator)
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-23099a72d800404cb755d54f4a419377
出典データセット
uspto-grants-2015_07
特許番号
US09085555B2

反応ノート

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