Thionyl Chloride → Methyl 4-chlorocinnoline-3-carboxylate

反応式

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]

参加物

反応物 2

HCID 24386Thionyl Chloride

HCID 178499158HCID 178499158、化合物

生成物 1

HCID 20187472Methyl 4-chlorocinnoline-3-carboxylate

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード: ord-d8e902608bc7424fb98797e5aed1d937
出典データセット: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07598247B2

反応ノート

読み込み中…

参加物