Hydrochloric Acid → HCID 178487268, compound

HRID 1749911Notes

Reaction equation

HRID 1749911 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([C:21]([O:23]C)=[O:22])=[C:19]([O:25][CH3:26])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1.CO.O.[OH-].[Li+].Cl>O.CS(C)=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([C:21]([OH:23])=[O:22])=[C:19]([O:25][CH3:26])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 178498961HCID 178498961, compound

Product 1

HCID 178487268HCID 178487268, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

Methyl (Z)-2-[(1H-indazol-3-yl)methylene]-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-carboxylate (0.070 g, 0.20 mmol) was added with methanol (3.0 mL), dimethyl sulfoxide (1.0 mL), and water (0.50 mL), and then added with lithium hydroxide monohydrate (0.025 g, 0.60 mmol), and the mixture was stirred at 30° C. for 10 hours. The reaction mixture was made acidic with 3 N hydrochloric acid, and the solid formed was collected by filtration. The solid was suspended in chloroform/methanol (95:5), then collected by filtration and dried to obtain (Z)-2-[(1H-indazol-3-yl)methylene]-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-carboxylic acid (0.045 g, 67%).

Workup

  1. customthe solid formed
  2. filtrationwas collected by filtration
  3. filtrationcollected by filtration
  4. customdried

Sources & evidence

ORD record
ord-9e7d790bd2b44117bfbf3c80c50833f9
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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