Phosphorus oxychloride → 8-Chloro-2-methyl-1,5-naphthyridine

반응식

[CH3:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2O.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:5]1[CH:6]=[CH:7][N:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2

참가 물질

반응물 2

HCID 24813Phosphorus oxychloride

HCID 1784233686-Methyl-1,5-naphthyridin-4-ol

생성물 1

HCID 6013988-Chloro-2-methyl-1,5-naphthyridine수율 67%

실험 절차

The suspension of 6-methyl-[1,5]naphthyridin-4-ol (1.60 g, 9.99 mmol) in POCl3 (25 mL) was heated under refluxing for 2 hrs. After cooling to room temperature, the reaction mixture was quenched with ice water and basified with NH4OH followed by extraction with AcOEt. The organic layer was washed with brine and dried over NaSO4, and concentrated to give 8-chloro-2-methyl-[1,5]naphthyridine as a brown solid (1.2 g, 67%). HR-MS-EI (+) m/e calcd for C9H7N2Cl (M+) 178.0298. found 178.0297.

후처리

temperaturewas heated
temperatureunder refluxing for 2 hrs
customthe reaction mixture was quenched with ice water
extractionfollowed by extraction with AcOEt
washThe organic layer was washed with brine
dry with materialdried over NaSO4
concentrationconcentrated

출처 및 근거

ORD 기록: ord-a158cea1f85541cea529233d3a545bfb
출처 데이터셋: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07304074B2

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