Methanol → Ethyl 2-methoxyquinoline-7-carboxylate

HRID 711071노트

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HRID 711071 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[N+:13]2[O-])=[CH:8][CH:7]=1)=[O:5])[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(N(CC)CC)C.[CH3:35][OH:36]>>[CH3:35][O:36][C:12]1[CH:11]=[CH:10][C:9]2[C:14](=[CH:15][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=2)[N:13]=1

참가 물질

5

반응물 4

HCID 887MethanolHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2회HCID 674915557-(Ethoxycarbonyl)quinoline 1-oxide

생성물 1

HCID 67491407Ethyl 2-methoxyquinoline-7-carboxylate수율 81%

실험 절차

To a 0° C. solution of 7-(ethoxycarbonyl)quinoline 1-oxide (150 mg, 0.69 mmol) and toluene-4-sulphonyl chloride (171 mg, 0.89 mmol) in methanol (5 mL) was added triethylamine (0.19 mL, 1.4 mmol). The reaction was stirred at room temperature overnight. LCMS showed the reaction was incomplete. Additional triethylamine (0.05 mL) was added and the reaction was stirred for another 4 hours. The reaction was concentrated and the residue partitioned between ethyl acetate and saturated aqueous sodium carbonate. The layers were separated and the aqueous was extracted two more times with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (0-40% ethyl acetate/heptanes) gave the title compound (130 mg, 81%) as a pale yellow solid. +ESI (M+H) 232.2; 1H NMR (400 MHz, CDCl3, δ): 8.49-8.60 (m, 1H), 7.95-8.05 (m, 2H), 7.75 (d, J=8.19 Hz, 1H), 6.98 (d, J=8.78 Hz, 1H), 4.43 (q, J=7.22 Hz, 2H), 4.08 (s, 3H), 1.43 (t, J=7.12 Hz, 3H).

후처리

  1. stirringthe reaction was stirred for another 4 hours
  2. concentrationThe reaction was concentrated
  3. customthe residue partitioned between ethyl acetate and saturated aqueous sodium carbonate
  4. customThe layers were separated
  5. extractionthe aqueous was extracted two more times with ethyl acetate
  6. washThe combined organics were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by flash column chromatography (0-40% ethyl acetate/heptanes)

출처 및 근거

ORD 기록
ord-cd9fabc726c24ae7a8d602cc495d9ef6
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181252B2

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