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4,6-Dichloro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile → 4,6-Dichloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

HRID 901275
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인쇄 미리보기

반응식

HRID 901275 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5](CC2C=CC(OC)=CC=2)[C:4](=[O:22])[C:3]=1[C:23]#[N:24]>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[NH:5][C:4](=[O:22])[C:3]=1[C:23]#[N:24]
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참가 물질

3

반응물 1

HCID 692163924,6-Dichloro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile

생성물 1

HCID 692174464,6-Dichloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile수율 96%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

4,6-dichloro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carbonitrile (95) (8.2 g, 22.70 mmol) in neat TFA was refluxed for 24 h. The solution was cooled and excess TFA was distilled off under reduced pressure. The residue was taken in water, basified by solid NaHCO3 and filtered. The solids were washed with excess water and dried to yield 5.2 g (96%) of 4,6-dichloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carbonitrile (97) as yellow solids. MP: 247° C.; 1H-NMR (DMSO-d6): δ 8.45 (dd, J=2.4 Hz, 1H), 8.82 (d, J=2.4 Hz, 1H), 13.17 (S, 1H); EIMS: 240 (M).

후처리

  1. temperatureThe solution was cooled
  2. distillationexcess TFA was distilled off under reduced pressure
  3. filtrationfiltered
  4. washThe solids were washed with excess water
  5. customdried

출처 및 근거

ORD 기록
ord-2db0ae8b238c4f8797d6b44e873a952d
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07361760B2

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