Sodium Hydroxide → HCID 58962839, compound

HRID 917734Notes

Reaction equation

HRID 917734 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([I:28])[CH:25]=[CH:24][C:3]=1[NH:4][C:5]1[C:6]([C:19]([O:21]CC)=[O:20])=[CH:7][N:8]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[C:9](=[O:11])[CH:10]=1.[OH-].[Na+]>CCO>[F:1][C:2]1[CH:27]=[C:26]([I:28])[CH:25]=[CH:24][C:3]=1[NH:4][C:5]1[C:6]([C:19]([OH:21])=[O:20])=[CH:7][N:8]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[C:9](=[O:11])[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23631096HCID 23631096, compound

Product 1

HCID 58962839HCID 58962839, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(2-fluoro-4-iodoanilino)-1-[2-(2-methoxyethoxy)ethyl]-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)-1-[2-(2-methoxyethoxy)ethyl]-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid as a cream solid (99%), used directly in the next step. 1H NMR [(CD3)2SO, 400 MHz] δ 13.00 (v br s, 1H), 9.72 (br s, 1H), 8.41 (s, 1H), 7.75 (dd, J=10.1, 1.9 Hz, 1H), 7.60 (ddd, J=8.3, 1.9, 0.8 Hz, 1H), 7.32 (t, J=8.5 Hz, 1H), 5.47 (d, 1.2 Hz, 1H), 4.05 (t, J=5.2 Hz, 2H), 3.60 (t, J=5.2 Hz, 2H), 3.53-3.50 (m, 2H), 3.42-3.38 (m, 2H), 3.21 (s, 3H). HRMS (EI+) calcd C17H18FIN2O5 (M+) 476.0245, found 476.0236.

Sources & evidence

ORD record
ord-1cbd60187ba94695bd9229ce46880f8c
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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