Sodium Hydroxide → 1-Ethyl-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

HRID 917730Notes

Reaction equation

HRID 917730 reaction equation
[CH2:1]([N:3]1[C:8](=[O:9])[CH:7]=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=2[F:18])[C:5]([C:19]([O:21]CC)=[O:20])=[CH:4]1)[CH3:2].[OH-].[Na+]>CCO>[CH2:1]([N:3]1[C:8](=[O:9])[CH:7]=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=2[F:18])[C:5]([C:19]([OH:21])=[O:20])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23631095Ethyl 1-ethyl-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate

Product 1

HCID 589628421-Ethyl-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-ethyl-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate was dissolved in EtOH and treated with 1 M NaOH, as for example 1, step C, to hydrolyse the ester to give 1-ethyl-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid as a white solid (100%), used directly in the next step. 1H NMR [(CD3)2SO, 400 MHz] δ 13.13 (v br s, 1H), 9.66 (br s, 1H), 8.49 (s, 1H), 7.75 (dd, J=10.1, 1.9 Hz, 1H), 7.59 (ddd, J=8.4, 2.0, 0.9 Hz, 1H), 7.31 (t, J=8.5 Hz, 1H), 5.49 (s, 1H), 3.91 (q, J=7.1 Hz, 2H), 1.19 (t, J=7.1 Hz, 3H). HRMS (EI+) calcd C14H12FIN2O3 (M+) 401.9877, found 401.9872.

Sources & evidence

ORD record
ord-ee33622f52324027b86aeaac69bed842
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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