Phosphorus oxychloride → 4-chloro-5H,6H,7H-cyclopenta[b]pyridine

반응식

[N+:1]1([O-])[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][CH2:8][CH2:9][C:2]=12.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:4]1[CH:5]=[CH:6][N:1]=[C:2]2[CH2:9][CH2:8][CH2:7][C:3]=12

참가 물질

반응물 2

HCID 24813Phosphorus oxychloride

HCID 131533156,7-Dihydro-5H-cyclopenta[b]pyridine 1-oxide

생성물 1

HCID 122033274-chloro-5H,6H,7H-cyclopenta[b]pyridine수율 94%

반응 조건

온도: 120 °C

실험 절차

6,7-Dihydro-5H-cyclopenta[b]pyridine 1-oxide (2.5 g, 18 mmol) was mixed with phosphoryl chloride (20 mL, 200 mmol). The reaction mixture was stirred at 120° C. for 3 h. The excess POCl3 was removed under reduced pressure. The residue was diluted in 80 mL of EtOAc and neutralized with Na2CO3 solution. After filtration, the aqueous layer was extracted with EtOAc twice. The combined organic extracts were dried, filtered and concentrated under reduced pressure to give the sub-title compound (2.6 g, 93%). LCMS calc. for C8H9ClN (M+H)+: m/z=154.2. Found: 154.3.

후처리

customThe excess POCl3 was removed under reduced pressure
additionThe residue was diluted in 80 mL of EtOAc and neutralized with Na2CO3 solution
filtrationAfter filtration
extractionthe aqueous layer was extracted with EtOAc twice
customThe combined organic extracts were dried
filtrationfiltered
concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록: ord-5dd0709017394eb7a3f7935c286067bf
출처 데이터셋: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09278950B2

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