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

HRID 917732Notes

Reaction equation

HRID 917732 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([I:24])[CH:21]=[CH:20][C:3]=1[NH:4][C:5]1[C:6]([C:15]([O:17]CC)=[O:16])=[CH:7][N:8]([CH2:12][CH2:13][CH3:14])[C:9](=[O:11])[CH:10]=1.[OH-].[Na+]>CCO>[F:1][C:2]1[CH:23]=[C:22]([I:24])[CH:21]=[CH:20][C:3]=1[NH:4][C:5]1[C:6]([C:15]([OH:17])=[O:16])=[CH:7][N:8]([CH2:12][CH2:13][CH3:14])[C:9](=[O:11])[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23630803Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1-propyl-1,6-dihydro-3-pyridinecarboxylate

Product 1

HCID 589628674-(2-Fluoro-4-iodoanilino)-6-oxo-1-propyl-1,6-dihydro-3-pyridinecarboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1-propyl-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-propyl-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), 9.70 (br s, 1H), 8.46 (s, 1H), 7.75 (dd, J=10.1, 1.9 Hz, 1H), 7.59 (ddd, J=8.4, 2.0, 0.8 Hz, 1H), 7.33 (t, J=8.5 Hz, 1H), 5.49 (s, 1H), 3.84 (t, J=7.2 Hz, 2H), 1.61 (sextet, J=7.4 Hz, 2H), 0.85 (t, J=7.4 Hz, 3H). HRMS (EI+) calcd C15H14FIN2O3 (M+) 416.0033, found 416.0036.

Sources & evidence

ORD record
ord-5655b8d6726741d0a19e6e345ed681cc
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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