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.O=P(Cl)(Cl)[Cl:13]>>[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 93%

반응 조건

온도: 120 °C

실험 절차

6,7-Dihydro-5H-cyclopenta[b]pyridine 1-oxide (2.5 g, 18 mmol) was mixed with POCl3 (20 mL). The reaction mixture was stirred at 120° C. for 3 h. The excess POCl3 was removed under reduced pressure. The residue was diluted in EtOAc (80 mL) and neutralized with aq. Na2CO3. After filtration, the aqueous layer was extracted with EtOAc twice. The combined organic layers 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=154.0. Found: 154.3.

후처리

customThe excess POCl3 was removed under reduced pressure
additionThe residue was diluted in EtOAc (80 mL)
filtrationAfter filtration
extractionthe aqueous layer was extracted with EtOAc twice
customThe combined organic layers were dried
filtrationfiltered
concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록: ord-46da843332ba4d9cb87df6ad4e5e9a03
출처 데이터셋: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09200004B2

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