Sodium Hydroxide → HCID 12851860, compound

HRID 1156896Notes

Reaction equation

HRID 1156896 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:19][C:20]([O:22]CC)=[O:21])[C:13]=3[CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[CH3:25][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:19][C:20]([OH:22])=[O:21])[C:13]=3[CH:12]=[CH:11][N:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12851861HCID 12851861, compound

Product 1

HCID 12851860HCID 12851860, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-(4-dimethylaminophenyl)isoquinoline-5-acetate (0.5 g) was heated for 1.5 hours with 40 ml of ethanol and 4 ml of a 5 N aqueous solution of sodium hydroxide. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, and it was treated with activated carbon. Acetic acid was added to acidify the treated residue. Yellow crystals which precipitated were collected by filtration, dried, and then recrystallized from tetrahydrofuran-acetone to afford 0.35 g of 1-(4-dimethylaminophenyl)isoquinoline-5-acetic acid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionWater was added to the residue, and it
  3. additionwas treated with activated carbon
  4. additionAcetic acid was added
  5. customYellow crystals which precipitated
  6. filtrationwere collected by filtration
  7. customdried
  8. customrecrystallized from tetrahydrofuran-acetone

Sources & evidence

ORD record
ord-759accc5709248ef86c882f4743ed7f5
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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