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

HRID 917706Notes

Reaction equation

HRID 917706 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4d0a4d2e1ba8467dace21b4e510a4bec
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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