Sulfuric Acid → 7,7-Dimethyl-8-fluorodibenzo[de,h]quinoline

HRID 84136Notes

Reaction equation

HRID 84136 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][N:13]=1)(O)[CH3:3].OS(O)(=O)=O.[OH-].[Na+]>ClC1C=CC=CC=1Cl>[CH3:1][C:2]1([CH3:3])[C:5]2[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=2[C:12]2[N:13]=[CH:14][CH:15]=[C:16]3[CH:17]=[CH:18][CH:19]=[C:20]1[C:21]=23

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 595226581-[2-(1-Methyl-1-hydroxyethyl)-3-fluorophenyl]isoquinoline

Product 1

HCID 569492497,7-Dimethyl-8-fluorodibenzo[de,h]quinolineYield 75.5%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

26.1 g (92.82 mmol) of 1-[2-(1-methyl-1-hydroxyethyl)-3-fluorophenyl]isoquinoline were added to a mixture at 150° C. of 260 ml of o-dichlorobenzene and 104.2 ml of H2SO4, and stirred for 60 min. The reaction solution was subsequently poured onto 1000 ml of ice and adjusted cautiously to pH=12 with solid NaOH with ice cooling. Subsequently, the mixture was extracted with 500 ml of dichloromethane, dried over MgSO4 and concentrated under reduced pressure. The crude product was dissolved in 100 ml of toluene and air was introduced at 50° C. for 4 h. Subsequently, purification was effected by column chromatography with dichloromethane. 18.45 g of a solid were obtained, corresponding to 75.5% of theory, with a purity of 99.6%.

Workup

  1. extractionSubsequently, the mixture was extracted with 500 ml of dichloromethane
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe crude product was dissolved in 100 ml of toluene
  5. additionair was introduced at 50° C. for 4 h
  6. customSubsequently, purification

Sources & evidence

ORD record
ord-f3c426f209f3454786741646076b5238
Source dataset
uspto-grants-2014_09
Patent number
US08846920B2

Reaction notes

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