Sodium Hydroxide → 8-Fluoro-2-methylquinolin-7-ol

HRID 339001Notes

Reaction equation

HRID 339001 reaction equation
[F:1][C:2]1[C:3]([O:13]C)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.B(Br)(Br)Br.[OH-].[Na+]>ClCCl>[F:1][C:2]1[C:3]([OH:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 867075048-Fluoro-7-methoxy-2-methylquinoline

Product 1

HCID 1363380788-Fluoro-2-methylquinolin-7-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 8-fluoro-7-methoxy-2-methylquinoline (0.57 g, 2.96 mmol) was stirred in dichloromethane (5 mL) and treated with a 1M solution of BBr3 in dichloromethane (15 mL). The resulting mixture was heated at reflux for 16 hours, then poured into crushed ice and basified with a 6N NaOH solution to pH 14. The organic layer was separated and the aqueous layer was further extracted with dichloromethane. The organic layer was pH adjusted to 6 with aqueous 6N HCl and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure to afford 8-fluoro-2-methylquinolin-7-ol in quantitative yield.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 16 hours
  3. additionpoured
  4. custominto crushed ice
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was further extracted with dichloromethane
  7. extractionextracted with ethyl acetate
  8. dry with materialThe combined organic extracts were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2e5b5e95f5f49f6bd210fdca1a95910
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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