Phosphorus oxychloride → Methyl 5-chlorobenzo[c][2,6]naphthyridine-8-carboxylate

HRID 604352ノート

反応式

HRID 604352 の反応式
O=[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:5]2[CH:12]=[CH:13][C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:15][C:4]=2[NH:3]1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:5]2[CH:12]=[CH:13][C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:15][C:4]=2[N:3]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 50942139Methyl 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-8-carboxylate

生成物 1

HCID 25252836Methyl 5-chlorobenzo[c][2,6]naphthyridine-8-carboxylate

実験手順

Methyl 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-8-carboxylate (200 mg, 0.787 mmol) was combined with phosphorus oxychloride (1 mL) and heated to reflux. After 2 hours, LCMS indicated the absence of any starting material. The volatiles were removed under reduced pressure. The residue was taken up in dichloromethane (50 mL) and washed twice with saturated aqueous sodium bicarbonate. The organic phase was dried over sodium sulfate and concentrated on a rotary evaporator to give methyl 5-chlorobenzo[c][2,6]naphthyridine-8-carboxylate (140 mg) as a grayish solid. LCMS (ESI) 273.3 (M+1)+.

後処理

  1. temperatureheated to reflux
  2. customThe volatiles were removed under reduced pressure
  3. washwashed twice with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated on a rotary evaporator

出典と根拠

ORDレコード
ord-92ed3472fba341c8b155e20da6b1abe2
出典データセット
uspto-grants-2011_03
特許番号
US07910600B2

反応ノート

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