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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
ノート
印刷プレビュー

反応式

HRID 901275 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2db0ae8b238c4f8797d6b44e873a952d
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07361760B2

反応ノート

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