Hydrochloric Acid → HCID 54724176, compound

HRID 1832078Notes

Reaction equation

HRID 1832078 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17]CC3C=CC(F)=CC=3F)=[C:12](Br)[C:11]2=[O:28])=[C:6]([Cl:29])[CH:5]=1.Cl>C1COCC1.O>[Cl:29][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[N:10]1[C:15]([CH3:16])=[CH:14][C:13]([OH:17])=[CH:12][C:11]1=[O:28])[C:3]([O:2][CH3:1])=[O:30]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22050037HCID 22050037, compound

Product 1

HCID 54724176HCID 54724176, compoundYield 110.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl-4-[3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-3-chlorobenzoate (2.30 g, 4.61 mmol) was taken up in THF (20 ml) and H2O (4 ml). 2.5 N NAOH (9.2 ml) was added to the vessel and the reaction stirred overnight to completion. Concentrated HCl was added dropwise until reaction was made acidic (pH=1). H2O (100 ml) and THF (100 ml) were added to the mixture. The contents were poured into a separatory funnel and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over Na2SO4, the solvent removed in vacuo, and the residue was taken up in a 50% mixture of ethyl acetate/hexane. The precipitate was collected on a filter pad to yield a white powder (1.5 g, 67%). 1H NMR (300 MHz, DMSO) δ 13.59 (1H), 8.16 (d, J=1.81 Hz, 1H), 8.06 (dd, J=6.24, 1.81 Hz, 1H), 7.73 (app q, J=8.46, 1H), 7.68 (d, J=8.26 Hz, 1H), 7.38 (dt, J=9.48, 2.62 Hz, 1H), 7.26-7.18 (m, 1H), 6.80 (s, 1H), 5.39 (s, 2H), 3.93 (s, 3H), 1.96 (s, 3H); ES-MS m/z 483 (M+H). ES-HRMS m/z 483.9749 (M+H calcd for C20H14BrClF2NO4 requires 483.9757).

Workup

  1. addition2.5 N NAOH (9.2 ml) was added to the vessel
  2. additionThe contents were poured into a separatory funnel
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent removed in vacuo
  6. customThe precipitate was collected on a filter pad

Sources & evidence

ORD record
ord-48d03419a4cd445c90beddce0bd81b19
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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