Sodium Hydroxide → 6-Bromo-3-cyano-2-methoxyquinoline

HRID 986006Notes

Reaction equation

HRID 986006 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]#[N:14])=[CH:5]2.F[B-](F)(F)F.[CH3:20][O+](C)C.[OH-].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH3:20])[C:6]([C:13]#[N:14])=[CH:5]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 142210276-Bromo-2-oxo-1,2-dihydroquinoline-3-carbonitrile

Product 1

HCID 142209686-Bromo-3-cyano-2-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 6-bromo-3-cyano-2-[1H]-quinolone (14.6 g) in dichloromethane (150 cm3) was stirred under nitrogen with trimethyloxonium tetrafluoroborate (10.35 g) for 2 days. A solution of 2M sodium hydroxide (100 cm3) was added and the aqueous phase was extracted with dichloromethane (3×200 cm3). The dried (MgSO4) extracts were concentrated in vacuo and the residue chromatographed on silica (Merck "MK 60.9385") eluting with hexane:ethyl acetate, 4:1, to give a solid which was recrystallised from ethyl acetate to afford 6-bromo-3-cyano-2-methoxyquinoline, m.p. 169°-172°, (1.96 g).

Workup

  1. extractionthe aqueous phase was extracted with dichloromethane (3×200 cm3)
  2. dry with materialThe dried (MgSO4) extracts
  3. concentrationwere concentrated in vacuo
  4. customthe residue chromatographed on silica (Merck "MK 60.9385")
  5. washeluting with hexane
  6. customethyl acetate, 4:1, to give a solid which
  7. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-4565d220923e40739968cfd05f479816
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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