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

HRID 917707Notes

Reaction equation

HRID 917707 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([I:21])[CH:18]=[CH:17][C:3]=1[NH:4][C:5]1[C:6]([C:12]([O:14]CC)=[O:13])=[CH:7][NH:8][C:9](=[O:11])[CH:10]=1.[OH-].[Na+]>CCO>[F:1][C:2]1[CH:20]=[C:19]([I:21])[CH:18]=[CH:17][C:3]=1[NH:4][C:5]1[C:6]([C:12]([OH:14])=[O:13])=[CH:7][NH:8][C:9](=[O:11])[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23630800Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate

Product 1

HCID 236310074-(2-Fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acidYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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 4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid as a white solid (99%), used directly in the next step. 1H NMR [(CD3)2SO, 400 MHz] δ 13.30 (v br s, 1H), 11.44 (br s, 1H), 9.75 (br s, 1H), 8.06 (s, 1H), 7.76 (dd, J=10.2, 1.9 Hz, 1H), 7.59 (ddd, J=8.3, 1.9, 0.9 Hz, 1H), 7.32 (t, J=8.4 Hz, 1H), 5.40 (d, J=1.1 Hz, 1H). LCMS (APCI+) calcd for C12H9FIN2O3 375 (MH+), found 375.

Sources & evidence

ORD record
ord-f973cebd13a0453e934d82bafaad8f5e
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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