Dimethylformamide → Ethyl 1-ethyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2099121노트

반응식

HRID 2099121 반응식
[I:1][C:2]1[CH:3]=[C:4]2C(=[CH:10][CH:11]=1)NC=[C:6]([C:12]([OH:14])=[O:13])[C:5]2=[O:15].[C:16](=O)([O-])[O-].[K+].[K+].I[CH2:23][CH3:24].[CH3:25][N:26]([CH:28]=O)[CH3:27]>C(OCC)(=O)C>[CH2:23]([O:14][C:12]([C:6]1[C:5](=[O:15])[C:4]2[C:27](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=2)[N:26]([CH2:25][CH3:16])[CH:28]=1)=[O:13])[CH3:24]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 7196836-Iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

생성물 1

HCID 57720090Ethyl 1-ethyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

A mixture of 1,4-dihydro-6-iodo-4-oxo-quinoline-3-carboxylic acid (J. Ellis et al, Aust. J. Chem., 1973, 26, 907) (3.15 g, 10 mmol), potassium carbonate (6.9 g, 50 mmol) and iodoethane (15.6 g, 100 mmol) in dry DMF was heated at 70° C. with vigorous stirring. After 16 h the mixture was cooled and diluted with ethyl acetate. The resultant mixture was washed with water and the organic phase separated, dried and evaporated to yield the title compound as pale yellow solid, 1H NMR δ (CDCl3) 1.41 (3H, t, J=7.1 Hz), 1.54 (3H, t, J=7.3 Hz), 4.23 (2H, q, J=7.2 Hz), 4.40 (2H, q, J=7.1 Hz), 7.20 (1H, d, J=8.9 Hz), 7.95 (1H, dd, J=2.1 & 8.9 Hz), 8.48 (1H, s), 8.86 (1H, d, J=2.1 Hz).

후처리

  1. temperatureAfter 16 h the mixture was cooled
  2. washThe resultant mixture was washed with water
  3. customthe organic phase separated
  4. customdried
  5. customevaporated

출처 및 근거

ORD 기록
ord-f0912f4223c140528fab2fb1983503f1
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569550B2

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