Citric Acid → HCID 59473759, compound

HRID 2069838Notes

Reaction equation

HRID 2069838 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[CH:15]=[C:14]([CH3:16])[C:6]([C:7](/[N:9]=[CH:10]/N(C)C)=[O:8])=[C:5]([F:17])[CH:4]=1.CC(C)([O-])C.[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:1][N:2]([CH3:18])[C:3]1[CH:15]=[C:14]2[C:6](=[C:5]([F:17])[CH:4]=1)[C:7](=[O:8])[NH:9][CH:10]=[CH:16]2

Participants

5

Reactant 3

HCID 311Citric AcidHCID 23665647Potassium tert-butoxideHCID 178428505HCID 178428505, compound

Product 1

HCID 59473759HCID 59473759, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the clear solution of 4-Dimethylamino-N-[1-dimethylamino-meth-(E)-ylidene]-2-fluoro-6-methyl-benzamide (0.709 g, 2.82 mmol) in THF (2 mL) was added potassium tert-butoxide (2.8 mL, 1.0 M THF, 1.0 eq.), and the resultant brown, homogeneous reaction mixture was refluxed. After 1 h., the reaction mixture was quenched with 1M citric acid (1 eq.), dried (MgSO4), filtered, and concentrated in vacuo to give a yellow solid, which was purified by preparative plate (50% 60/10/1 CH2Cl2/MeOH/NH4OH in CH2Cl2) to give 6-Dimethylamino-8-fluoro-2H-isoquinolin-1-one as a white solid (0.104 g, 18%).

Workup

  1. temperaturethe resultant brown, homogeneous reaction mixture was refluxed
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a yellow solid, which
  6. customwas purified by preparative plate (50% 60/10/1 CH2Cl2/MeOH/NH4OH in CH2Cl2)

Sources & evidence

ORD record
ord-e80971a62af64ee6a1fbfa6851645200
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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