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

HRID 1061500노트

반응식

HRID 1061500 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 222840352-Chloro-5-fluoropyridin-4-amine수율 91%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-24e236fa91f74f8cb09f083efcc9a204
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960568B2

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