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

HRID 2174886노트

반응식

HRID 2174886 반응식
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

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-c8597179cb84417585a37ab0bf1f8f3b
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062043B2

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