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

HRID 2099121ノート

反応式

HRID 2099121 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f0912f4223c140528fab2fb1983503f1
出典データセット
uspto-grants-2009_08
特許番号
US07569550B2

反応ノート

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