Peracetic Acid → 7-(Ethoxycarbonyl)quinoline 1-oxide

HRID 880949ノート

反応式

HRID 880949 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(OO)(=[O:18])C>ClCCl>[CH2:14]([O:13][C:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH:4]=[CH:3][CH:2]=[N+:1]2[O-:18])=[CH:6][CH:7]=1)=[O:12])[CH3:15]

参加物

4

反応物 2

HCID 6585Peracetic AcidHCID 3799493Ethyl Quinoline-7-carboxylate

生成物 1

HCID 674915557-(Ethoxycarbonyl)quinoline 1-oxide収率 92.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of ethyl quinoline-7-carboxylate (1.02 g, 5.05 mmol) in dichloromethane (20 mL) was added peracetic acid (2.13 mL, 10.1 mmol, 32 wt % in acetic acid). The reaction was stirred at room temperature overnight. The reaction was partitioned between water and dichloromethane. The layers were separated and the aqueous was extracted with dichloromethane (4×). The combined organics were washed with water and brine, dried over sodium sulfate, filtered, and concentrated. The solid was concentrated from heptanes and ethyl acetate several times, then dried under vacuum to give the title compound (1.01 g, 92%) as a yellow solid. +ESI (M+H) 218.2; 1H NMR (400 MHz, CDCl3, δ): 9.40 (s, 1H), 8.65 (d, J=6.05 Hz, 1H), 8.27 (dd, J=8.58, 1.56 Hz, 1H), 7.95 (d, J=8.39 Hz, 1H), 7.82 (d, J=8.58 Hz, 1H), 7.42 (dd, J=8.49, 6.15 Hz, 1H), 4.47 (q, J=7.02 Hz, 2H), 1.45 (t, J=7.1 Hz, 3H).

後処理

  1. customThe reaction was partitioned between water and dichloromethane
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with dichloromethane (4×)
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationThe solid was concentrated from heptanes and ethyl acetate several times
  9. customdried under vacuum

出典と根拠

ORDレコード
ord-5659ecf08f5f4e9683fb55df0f4fb7c6
出典データセット
uspto-grants-2015_03
特許番号
US08993586B2

反応ノート

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