Sulfuric Acid → 9-Chloro-6-fluorobenzo[g]isoquinoline-5,10-dione

HRID 440358

Reaction equation

HRID 440358 reaction equation
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([F:23])=[C:11]([CH:22]=1)[CH2:12][C:13]1[C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=[CH:15][CH:14]=1>>[Cl:6][C:7]1[C:22]2[C:19](=[O:21])[C:18]3[CH:17]=[N:16][CH:15]=[CH:14][C:13]=3[C:12](=[O:2])[C:11]=2[C:10]([F:23])=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 199747604-(5-Chloro-2-fluorobenzyl)nicotinic acid

Product 1

HCID 108490269-Chloro-6-fluorobenzo[g]isoquinoline-5,10-dioneYield 82%

Conditions

Temperature
130 °C

Procedure

Fuming sulfuric acid (30% SO3 ; 0.31 mL) is added to 4-(5-chloro-2-fluorobenzyl)nicotinic acid of Preparative Example 12. The dark mixture is heated quickly to 130° C. for 10 min in a flask fitted with a cotton filled drying tube. After cooling to room temperature, the reaction mixture is quenched with ice (3 g) and extracted with methylene chloride (4×7 mL). The combined extracts are dried with Na2SO4 and the solvent is removed by roto-evaporation to yield 9-chloro-6-fluorobenzo[g]isoquinoline-5,10-dione as a yellow solid (0.045 g; 82% yield).

Workup

  1. customfitted with a cotton
  2. additionfilled
  3. customdrying tube
  4. temperatureAfter cooling to room temperature
  5. customthe reaction mixture is quenched with ice (3 g)
  6. extractionextracted with methylene chloride (4×7 mL)
  7. dry with materialThe combined extracts are dried with Na2SO4
  8. customthe solvent is removed by roto-evaporation

Sources & evidence

ORD record
ord-7f7e227ef147490d89c4a9bc1333d193
Source dataset
uspto-grants-1996_05
Patent number
US05519029

Linked notes

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