Acetic Anhydride → 2-Acetoxy-8-hydroxyquinoline

反応式

[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N+:10]([O-])=[CH:9][CH:8]=[CH:7]2.[C:13]([O:16]C(=O)C)(=[O:15])[CH3:14]>>[C:13]([O:16][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([OH:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=1)(=[O:15])[CH3:14]

参加物

反応物 2

HCID 7918Acetic Anhydride

HCID 143128-Hydroxyquinoline N-oxide

生成物 1

HCID 229959082-Acetoxy-8-hydroxyquinoline収率 84%

実験手順

A mixture of 5a (0.81 g, 5 mmol) in acetic anhydride (20 ml) was heated at reflux for 2 h (monitored by TLC). After cooling, it was poured into ice water (100 ml). The resulting solid was collected and crystallized from dichloromethane to give 2-Acetoxy-8-hydroxyquinoline (5b) (0.85 g, 84%) as white crystals. mp: 240°-241° C.; 1H-NMR (DMSO-d6): δ2.55; (s, 3H, CH3), 6.66 (d, 3-H), 7.15-7.23 (m, 3H, Ar--H), 7.78 (d, 4-H), 11.31 (br s, 1H, OH).

後処理

temperaturewas heated
temperatureat reflux for 2 h (monitored by TLC)
temperatureAfter cooling
customThe resulting solid was collected
customcrystallized from dichloromethane

出典と根拠

ORDレコード: ord-bc6e806dbf364725806bdc33ed6a059a
出典データセット: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US05646164

反応ノート

読み込み中…

参加物