Thionyl Chloride → Methyl 4-chlorocinnoline-3-carboxylate

반응식

S(Cl)([Cl:3])=O.O[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[N:8][C:7]=1[C:16]([O:18][CH3:19])=[O:17]>>[Cl:3][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[N:8][C:7]=1[C:16]([O:18][CH3:19])=[O:17]

참가 물질

반응물 2

HCID 24386Thionyl Chloride

HCID 178499158HCID 178499158, 화합물

생성물 1

HCID 20187472Methyl 4-chlorocinnoline-3-carboxylate

실험 절차

Thionyl chloride (8.15 g, 5 ml) was added dropwise under inert atmosphere to methyl 4-hydroxycinnoline-3-carboxylate (0.50 g, 2.45 mmol). The mixture was heated to reflux for 1.5 h, cooled to room temperature and excess thionyl chloride was removed under vacuum. Toluene (5 ml) was added to the residue. The mixture was stirred at room temperature overnight. The solids were collected by filtration and dried under vacuum. The title compound was isolated as a brown solid (248 mg, 1.11 mmol, 45%). LCMS: m/z 223 [M+H]+.

후처리

temperatureThe mixture was heated
temperatureto reflux for 1.5 h
customexcess thionyl chloride was removed under vacuum
additionToluene (5 ml) was added to the residue
filtrationThe solids were collected by filtration
customdried under vacuum

출처 및 근거

ORD 기록: ord-7a68a5a8db6e467db81839c9be13058d
출처 데이터셋: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08309552B2

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