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

HRID 917706노트

반응식

HRID 917706 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4d0a4d2e1ba8467dace21b4e510a4bec
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273877B2

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