Sodium Hydroxide → HCID 68953118, compound

HRID 2384888Notes

Reaction equation

HRID 2384888 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][C:13]3[CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=4)[S:18][C:12]=3[C:11]2=[O:26])=[CH:6][C:5]=1[O:27][CH3:28].[OH-].[Na+]>CO.O1CCCC1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[S:18][C:12]3[C:11](=[O:26])[N:10]([C:7]4[CH:8]=[CH:9][C:4]([C:3]([OH:29])=[O:2])=[C:5]([O:27][CH3:28])[CH:6]=4)[CH2:15][CH2:14][C:13]=3[CH:16]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68954408HCID 68954408, compound

Product 1

HCID 68953118HCID 68953118, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Suspend 4-[2-(4-chloro-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-2-methoxy-benzoic acid methyl ester (0.4 g, 0.94 mmol) in methanol (5 mL) and tetrahydrofuran (5 mL) and add 1 N NaOH (1.13 mL, 1.13 mmol). Heat the mixture at reflux for 16 h, cool to RT, and concentrate in vacuo. Suspend the residue in water (25 mL) and acidify with 10% sodium bisulfate. Extract the mixture with ethyl acetate (4×20 mL) to give a suspension in the organic portion. Filter the solid and dry in vacuo to give 0.19 g (49%) of the title compound. Concentrate the filtrate in vacuo to give 0.09 g (23%) more of the title compound. MS/ES m/z (35Cl) 414.0 [M+H]+.

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux for 16 h
  3. concentrationconcentrate in vacuo
  4. extractionExtract the mixture with ethyl acetate (4×20 mL)
  5. customto give a suspension in the organic portion
  6. filtrationFilter the solid
  7. customdry in vacuo

Sources & evidence

ORD record
ord-386e06848ae64e2192d96f8debefc591
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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