HCID 22048290, compound → HCID 11475349, compound

HRID 1833130Notes

Reaction equation

HRID 1833130 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:30]=[CH:31][CH:32]=1)[C:9]([C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[C:14]([C:25]([O:27]CC)=[O:26])=[CH:13][N:12]=1)=[O:10])[CH2:2][CH2:3][CH3:4]>C(O)C.C1COCC1.[OH-].[Na+]>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:30]=[CH:31][CH:32]=1)[C:9]([C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[C:14]([C:25]([OH:27])=[O:26])=[CH:13][N:12]=1)=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 1

HCID 22048290HCID 22048290, compound

Product 1

HCID 11475349HCID 11475349, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

The above intermediate, 1-(3-butoxybenzoyl)-6,7-dimethoxy-4-ethoxycarbonyl-isoquinoline (390 mg, 0.89 mmol) was dissolved in a solution of ethanol (10 ml), THF (5 ml) and 4N sodium hydroxide (1 ml). The mixture was refluxed until all starting material was consumed. Solvents were evaporated and 25 ml of water was added. The solution was washed with ethyl ether (2×10 ml). The aqueous phase was neutralized by the addition of 4 ml of 1.0 N hydrochloric acid. The milky mixture was extracted with two 25 ml portions of ethyl acetate. The organic layer was washed with brine. The organic extracts were dried over sodium sulfate, filtered and evaporated to give 350 mg of yellow solid which was stirred in 25 ml of ethyl ether. The solid was filtered and washed with cold ethyl ether to produce 310 mg of the carboxylic acid as a yellow solid 1-(3-Butoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid.

Workup

  1. temperatureThe mixture was refluxed until all starting material
  2. customwas consumed
  3. customSolvents were evaporated
  4. addition25 ml of water was added
  5. washThe solution was washed with ethyl ether (2×10 ml)
  6. additionThe aqueous phase was neutralized by the addition of 4 ml of 1.0 N hydrochloric acid
  7. extractionThe milky mixture was extracted with two 25 ml portions of ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialThe organic extracts were dried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-0312c34b274e44ff91e5fe835c755c70
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

Loading…