Hydrochloric Acid → 1,4-Dichloro-7-isoquinolinecarboxylic acid

HRID 2289818Notes

Reaction equation

HRID 2289818 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14]CC)=[O:13])[CH:10]=2)[C:5]([Cl:17])=[CH:4][N:3]=1.[OH-].[Na+].CCO.Cl>C1COCC1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=2)[C:5]([Cl:17])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 18698389Ethyl 1,4-dichloro-7-isoquinolinecarboxylate

Product 1

HCID 186982431,4-Dichloro-7-isoquinolinecarboxylic acidYield 53.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Anal. Found: C, 53.27; H, 3.48; N, 5.14. Calc for C12H9Cl2NO2 : C, 53.36; H, 3.36; N, 5.19. ##STR169## Ethyl 1,4-dichloro-7-isoquinolinecarboxylate (500 mg, 1.85 mmol) in THF (2 mL) was treated with an aqueous solution of NaOH (3.7 mL, 1 M) and EtOH (few drops) added to give a single phase mixture. After stirring at room temperature overnight, HCl (3.7 mL, 1 M) was added to give a thick slurry which was filtered off, washed with water, and crystallised from i-PrOH. The fluffy white crystalline solid was triturated with hexane and dried to afford 1,4-dichloro-7-isoquinolinecarboxylic acid (240 mg, 0.99 mmol).

Workup

  1. additionadded
  2. customto give a single phase mixture
  3. customto give a thick slurry which
  4. filtrationwas filtered off
  5. washwashed with water
  6. customcrystallised from i-PrOH
  7. customThe fluffy white crystalline solid was triturated with hexane
  8. customdried

Sources & evidence

ORD record
ord-5128d79f276c4620b6db8429ef5d0091
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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