Water → Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate

HRID 917706ノート

反応式

HRID 917706 の反応式
Cl[C:2]1[CH:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[F:21])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[OH2:22]>C(O)(=O)C>[F:21][C:15]1[CH:16]=[C:17]([I:20])[CH:18]=[CH:19][C:14]=1[NH:13][C:11]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][NH:3][C:2](=[O:22])[CH:12]=1

参加物

4

反応物 2

HCID 962WaterHCID 23631002Ethyl 6-chloro-4-(2-fluoro-4-iodoanilino)nicotinate

生成物 1

HCID 23630800Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate収率 59%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Ethyl 6-chloro-4-(2-fluoro-4-iodoanilino)nicotinate (2.03 g, 4.83 mmol) was dissolved in acetic acid (75 mL), to which was added water (25 mL). This solution was heated at reflux for 14 h. The mixture was allowed to cool, then refrigerated, and a cream solid crystallised out. This material was isolated by filtration, washed well with water and hexanes, then dried to afford ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate as a white solid (1.14 g, 59%), m.p. (acetone/MeOH) 262-264° C. 1H NMR [(CD3)2SO, 400 MHz] δ 11.59 (br s, 1H), 9.32 (s, 1H), 8.10 (s, 1H), 7.77 (dd, J=10.1, 1.9 Hz, 1H), 7.61 (ddd, J=8.4, 2.0, 0.8 Hz, 1H), 5.38 (d, J=1.3 Hz, 1H), 7.26-7.33 (m, 1H), 4.27 (q, J=7.1 Hz, 2H), 1.30 (t, J=7.1 Hz, 3H). Anal. Calcd for C14H12FIN2O3: C, 41.8; H, 3.0; N, 7.0. Found: C, 41.9; H, 2.8; N, 7.0.

後処理

  1. temperatureThis solution was heated
  2. temperatureat reflux for 14 h
  3. temperatureto cool
  4. customa cream solid crystallised out
  5. customThis material was isolated by filtration
  6. washwashed well with water and hexanes
  7. customdried

出典と根拠

ORDレコード
ord-4d0a4d2e1ba8467dace21b4e510a4bec
出典データセット
uspto-grants-2007_09
特許番号
US07273877B2

反応ノート

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