Methanol → 3-Fluoro-7-hydroxy-2-methylquinoline

HRID 454136Notes

Reaction equation

HRID 454136 reaction equation
[F:1][C:2]1[C:3]([CH3:14])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12]C)[CH:6]=2.B(Br)(Br)Br.CO>ClCCl>[F:1][C:2]1[C:3]([CH3:14])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([OH:12])[CH:6]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 220307923-Fluoro-7-methoxy-2-methylquinoline

Product 1

HCID 1357631233-Fluoro-7-hydroxy-2-methylquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Fluoro-7-methoxy-2-methylquinoline (0.16 g, 0.85 mmol) was taken up in dichloromethane (4 ml) under nitrogen and treated with boron tribromide solution (4 ml of a 1.0M solution in dichloromethane, 4.0 mmol). The reaction was stirred for 24 hours at ambient temperature followed by the slow addition of excess methanol. The solution was stirred for a further 2 hours and then evaporated to dryness to give 3-fluoro-7-hydroxy-2-methylquinoline which was used without further purification.

Workup

  1. stirringThe solution was stirred for a further 2 hours
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-1671a113e0e84df59dd109665832c08a
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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