Potassium Carbonate → Ethyl 6-iodo-1-(2-morpholinoethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2061872노트

반응식

HRID 2061872 반응식
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH2:9])[CH2:3][CH2:2]1.CN(C)/[CH:12]=[C:13](/[C:19](=[O:28])[C:20]1[CH:25]=[C:24]([I:26])[CH:23]=[CH:22][C:21]=1F)\[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>>[I:26][C:24]1[CH:25]=[C:20]2[C:21](=[CH:22][CH:23]=1)[N:9]([CH2:8][CH2:7][N:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:19]2=[O:28]

참가 물질

4

반응물 3

HCID 11430Potassium CarbonateHCID 4082852-MorpholinoethylamineHCID 70809441(Z)-ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate2회

생성물 1

HCID 59208337Ethyl 6-iodo-1-(2-morpholinoethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

반응 조건

온도
40 °C

실험 절차

2-Morpholinoethanamine (0.88 g, 6.7 mmol) was added to the stock solution of (Z)-ethyl 3-(dimethylamino)-2-(3-iodobenzoyl)acrylate (Intermediate 24, 0.38M, 18 mL, 7 mmol) and the mixture was heated at 40° C. for 3 h. The solvent was removed in vacuo and the resulting residue was dried in a vacuum oven for 1.5 h. The residue was then dissolved in dimethyl formamide (5 mL) and potassium carbonate powder (1.2 g, 10 mmol) was added. The reaction was heated at 70° C. for a further 3 h then cooled to room temperature. The crude reaction mixture was placed into a fridge for a 3 h. The solid precipitate that formed was collected by filtration, washed with a small amount of dimethylformamide, followed by water, then dried under high vacuum.

후처리

  1. customThe solvent was removed in vacuo
  2. customthe resulting residue was dried in a vacuum oven for 1.5 h
  3. dissolutionThe residue was then dissolved in dimethyl formamide (5 mL)
  4. temperatureThe reaction was heated at 70° C. for a further 3 h
  5. temperaturethen cooled to room temperature
  6. customThe crude reaction mixture
  7. customThe solid precipitate that formed
  8. filtrationwas collected by filtration
  9. washwashed with a small amount of dimethylformamide
  10. customdried under high vacuum

출처 및 근거

ORD 기록
ord-09b3707fcd324b05b3d0596494c6d70b
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283361B2

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