Sodium Hydroxide → HCID 19004371, compound

HRID 2225730Notes

Reaction equation

HRID 2225730 reaction equation
C[O:2][C:3](=[O:26])[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[CH:20][N:21]=[CH:22]3)=[CH:17][CH:16]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O1CCCC1.O>[CH:22]1[C:23]2[C:18](=[CH:17][CH:16]=[C:15]([O:14][CH2:13][CH2:12][O:11][C:8]3[CH:7]=[CH:6][C:5]([C:4](=[O:25])[C:3]([OH:26])=[O:2])=[CH:10][CH:9]=3)[CH:24]=2)[CH:19]=[CH:20][N:21]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 53634023HCID 53634023, compound

Product 1

HCID 19004371HCID 19004371, compoundYield 93.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[[2-(7-isoquinolyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester (0.5 g) in hot methanol (5 mL) and tetrahydrofuran (5 mL) was treated with 1N sodium hydroxide (2.0 mL) and diluted with water. The organic solvent was removed under vacuum and the residue was dissolved in hot water. Cold 2N hydrochloric acid (1.0 mL) was added dropwise and the product was allowed to crystallize and was filtered, washed with water and dried to give 0.45 g of 4-[[2-(7-isoquinolyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid as a colorless solid, mp 260° C. with decomposition.

Workup

  1. customThe organic solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in hot water
  3. additionCold 2N hydrochloric acid (1.0 mL) was added dropwise
  4. customto crystallize
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-7b665bbb7dd646de8338b584a7af930f
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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