Dichloromethane ethylacetate → 2-Chloro-5-fluoropyridin-4-amine

HRID 1061500ノート

反応式

HRID 1061500 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([F:11])=[CH:4][N+:3]=1[O-].C(Cl)Cl.CCOC(C)=O>[Ni].C(O)C>[NH2:8][C:6]1[C:5]([F:11])=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=1

参加物

5

反応物 2

HCID 21226138Dichloromethane ethylacetateHCID 222840222-Chloro-5-fluoro-4-nitro-1-oxo-1lambda~5~-pyridine

生成物 1

HCID 222840352-Chloro-5-fluoropyridin-4-amine収率 91%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

実験手順

A mixture of 2-chloro-5-fluoro-4-nitropyridine-1-oxide (11, 1.3 g, 6.8 mmol) and 1.6 g of Raney nickel in 80 mL of anhydrous ethyl alcohol was hydrogenated at 40 psi in a Parr hydrogenation apparatus for 3 h when TLC showed that the starting material had disappeared and a new spot was detected (CH2Cl2/EtOAc, 4:1, v/v, Rf0.78 and 0.71, for the starting material and the product, respectively). The catalyst was removed by filtration and washed carefully with ethyl alcohol. The filtrate and washings were combined and evaporated in vacuo to give 0.9 g (91%) of product as an off-white solid. A small analytical sample was purified by recrystallization from hot water to afford white crystals: mp 110-111° C.; 1H NMR (CDCl3) δ4.50 (br s, 2 H, NH2, D2O exchangeable), 7.15 (d, 1 H, 3-H, J=6 Hz), 7.95 (d, 1H, 6-H, J=2 Hz). Analysis calculated for C5H4ClFN2: C, 40.97; H, 2.75; N, 19.12. Found: C, 41.18; H, 2.39; N, 18.89.

後処理

  1. customThe catalyst was removed by filtration
  2. washwashed carefully with ethyl alcohol
  3. customevaporated in vacuo

出典と根拠

ORDレコード
ord-24e236fa91f74f8cb09f083efcc9a204
出典データセット
uspto-grants-2005_11
特許番号
US06960568B2

反応ノート

読み込み中…