Phosphorus oxychloride → 6-Chloro-2-methylnicotinonitrile

반응식

[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

참가 물질

반응물 2

HCID 24813Phosphorus oxychloride

HCID 113785166-Hydroxy-2-methylnicotinonitrile

생성물 1

HCID 123877376-Chloro-2-methylnicotinonitrile수율 54%

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록: ord-862b4a0dc048400e81b27ac8639aa589
출처 데이터셋: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09034870B2

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