Sodium Hydroxide → HCID 57300363, compound

HRID 868953Notes

Reaction equation

HRID 868953 reaction equation
[N+]([C:4]1[CH:5]=C(S([O-])(=O)=O)C=[CH:8][CH:9]=1)([O-])=O.[Na+].OS(O)(=O)=O.O=S(=O)=O.[F:24][C:25]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:26]=1[NH2:27].C(=O)/C=C/C.[OH-].[Na+]>O>[F:32][C:31]1[C:25]([F:24])=[C:26]2[C:28]([CH:5]=[CH:4][C:9]([CH3:8])=[N:27]2)=[CH:29][CH:30]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 24681Fuming sulfuric acidHCID 31389Sodium 3-nitrobenzenesulfonateHCID 782782,3-DifluoroanilineHCID 447466Crotonaldehyde

Product 1

HCID 57300363HCID 57300363, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

Sodium 3-nitrobenzenesulfonate (2.7 g, 12 mmol) was dissolved in H2O (3 mL), and oleum (4 mL) was added to the mixture. 2,3-Difluoroaniline was then added to the mixture. The mixture was heated to 105° C. and (E)-but-2-enal (2.34 g, 33.4 mmol) was added dropwise. The mixture was stirred at 120° C. for 1 h. Then the mixture was poured into ice (50 g), and solid NaOH was added until pH 12. The mixture was extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography to afford 7,8-difluoro-2-methylquinoline (1.5 g) as a white solid.

Workup

  1. additionwas added until pH 12
  2. extractionThe mixture was extracted with EtOAc (50 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-6871ce2aefd94edb9f13040a6079a666
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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