O-Methylhydroxylamine hydrochloride → HCID 62553448、化合物

HRID 2233424ノート

反応式

HRID 2233424 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=O)=[CH:3][CH:2]=1.Cl.O([NH2:20])C>FC(F)(F)C(O)=O.[Pd]>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH:8]([NH2:20])[C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=[CH:3][CH:2]=1

参加物

5

反応物 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 113562871-(3-Methylphenyl)-2-(pyridin-4-yl)ethan-1-one

生成物 1

HCID 62553448HCID 62553448、化合物

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 6422Trifluoroacetic acid溶媒

実験手順

The intermediate oxime was prepared from 2-pyridin-4-yl-1-m-tolyl-ethanone (crude) and methoxylamine hydrochloride (8.00 g, 95.78 mmol) according to the protocol described in general procedure B. The oxime was then dissolved in trifluoroacetic acid (30.00 mL) and Pd/C (0.80 g) was added. The reaction mixture was hydrogenated under 50 psi for 14 hours, then filtered and concentrated. The residue was basified with 5M sodium hydroxide and extracted with methylene chloride. The combined organic phases were dried over potassium carbonate and concentrated to yield the title compound. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.27 (s, 3H) 2.89 (d, J=7.04 Hz, 2 H) 4.12 (t, 1 H) 7.10-7.22 (m, 1 H) 7.39 (ddd, J=7.77, 4.25, 1.47 Hz, 2 H) 7.75-7.82 (m, 1H) 8.41 (td, J=4.98, 2.05 Hz, 2 H) 8.58 (dd, J=5.86, 1.76 Hz, 2 H).

後処理

  1. filtrationfiltered
  2. concentrationconcentrated
  3. extractionextracted with methylene chloride
  4. dry with materialThe combined organic phases were dried over potassium carbonate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-3d700f68197844d594d12233cbba9d89
出典データセット
uspto-grants-2010_05
特許番号
US07709507B2

反応ノート

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