Phosphorus oxychloride → 6-Chloro-2-methylnicotinonitrile

反応式

[CH3:1][C:2]1[NH:3][C:4](=O)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:4]1[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([CH3:1])[N:3]=1

参加物

反応物 2

HCID 24813Phosphorus oxychloride

HCID 113785166-Hydroxy-2-methylnicotinonitrile

生成物 1

HCID 123877376-Chloro-2-methylnicotinonitrile収率 54%

実験手順

A mixture of 131 (1.5 g, 11 mmol) and phosphorus oxychloride (9 mL, 0.1 mol) was heated at reflux for 6 h. The reaction mixture was cooled to room temperature, and the excess phosphorus oxychloride was removed under reduced pressure. Ice cold water (50 mL) was added to the residue. The brown precipitate was collected and washed with ice cold water (3×25 mL), ether (2×20 mL), and dried to provide 132 as a light-brown solid (0.9 g, 54%): mp 104-105° C. (lit. (Synthesis 1991, 894-896) mp 106-108° C.). 1HNMR (300 MHz, CDCl3) δ 7.83 (d, J=8.1 Hz, 1H), 7.29 (d, J=8.1 Hz, 1H), 2.77 (s, 3H).

後処理

temperaturewas heated
temperatureat reflux for 6 h
customthe excess phosphorus oxychloride was removed under reduced pressure
additionIce cold water (50 mL) was added to the residue
customThe brown precipitate was collected
washwashed with ice cold water (3×25 mL), ether (2×20 mL)
customdried

出典と根拠

ORDレコード: ord-862b4a0dc048400e81b27ac8639aa589
出典データセット: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09034870B2

反応ノート

読み込み中…

参加物