Phosphorus oxychloride → Methyl 2-chloroquinoline-4-carboxylate

HRID 457242

반응식

HRID 457242 반응식
[C:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=O)[CH:6]=1)([O:3][CH3:4])=[O:2].O=P(Cl)(Cl)[Cl:18]>C1(C)C=CC=CC=1>[Cl:18][C:7]1[CH:6]=[C:5]([C:1]([O:3][CH3:4])=[O:2])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 1816364-Quinolinecarboxylic acid, 1,2-dihydro-2-oxo-, methyl ester

생성물 1

HCID 5202936Methyl 2-chloroquinoline-4-carboxylate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A stirred solution of 4-carbomethoxy quinolin-2-one (prepared as shown in Method D (1.76 g, 9 mmol), POCl3 (4.6 g, 30 mmol) in toluene (40 mL) was heated at reflux for 2 h then allowed to cool to room temperature and poured into ice water (50 mL). The mixture was extracted with ethyl acetate (3×50 mL). The organics were combined, washed with water, brine, dried (MgSO4) and concentrated in vacuo to afford the desired 2-chloro-4-carbomethoxyquinoline lv (1.50 mg). 1H NMR (DMSO-d6) δ 8.54 (d, J=8 Hz, 1H), 8.03–8.06 (m, 1H), 7.89–7.94 (m, 2H), 7.75–7.77 (m, 1H), 3.98 (s, 3H); ESI-MS m/z 222.1 (100, M+H+).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b36a07f38eed4728aeaff17b4b8cd6b0
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186841B2

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