Sodium Hydroxide → HCID 58962840, compound

HRID 917736Notes

Reaction equation

HRID 917736 reaction equation
[CH2:1]([N:4]1[C:9](=[O:10])[CH:8]=[C:7]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=2[F:19])[C:6]([C:20]([O:22]CC)=[O:21])=[CH:5]1)[CH:2]=[CH2:3].[OH-].[Na+]>CCO>[CH2:1]([N:4]1[C:9](=[O:10])[CH:8]=[C:7]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=2[F:19])[C:6]([C:20]([OH:22])=[O:21])=[CH:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23630904HCID 23630904, compound

Product 1

HCID 58962840HCID 58962840, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-allyl-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-allyl-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 13.25 (v br s, 1H), 9.73 (br s, 1H), 8.41 (s, 1H), 7.75 (dd, J=10.1, 1.9 Hz, 1H), 7.60 (ddd, J=8.4, 2.0, 0.8 Hz, 1H), 7.32 (t, J=8.5 Hz, 1H), 5.98-5.86 (m, 1H), 5.49 (d, J=1.1 Hz, 1H), 5.19 (dd, J=10.3, 1.4 Hz, 1H), 5.14 (ddd, J=17.1, 3.0, 1.5 Hz, 1H), 4.52 (d, J=5.6 Hz, 2H). HRMS (EI+) calcd C15H12FIN2O3 (M+) 413.9877, found 413.9874.

Sources & evidence

ORD record
ord-2b8e8d3ae84240f7ac4fb2b5e99ec0e6
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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