Benzyl Bromide → HCID 15114590, compound

HRID 1757286Notes

Reaction equation

HRID 1757286 reaction equation
[H-].[Na+].Cl[C:4]1[CH:13]=[C:12]2[C:7]([C:8](=O)CC(CC)=N2)=[CH:6][CH:5]=1.[Cl:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[C:20](=[O:30])[CH2:21][C:22]([CH2:28][CH3:29])=[N:23]2.[H][H].C(Br)C1C=CC=CC=1>CN(C=O)C>[CH2:8]([O:30][C:20]1[C:19]2[C:24](=[CH:25][CH:26]=[CH:27][C:18]=2[Cl:17])[N:23]=[C:22]([CH2:28][CH3:29])[CH:21]=1)[C:7]1[CH:12]=[CH:13][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 67788617HCID 67788617, compoundHCID 67789697HCID 67789697, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15114590HCID 15114590, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil; 1.95 g) was added to a stirred solution of a mixture of 7-chloro-2-ethyl-4-quinolone and 5-chloro-2-ethyl-4-quinolone (43.5:56.5, 10 g) in DMF (100 ml). The mixture was stirred until evolution of hydrogen had ceased and benzylbromide (8.25 g) was added. The mixture was stirred for 18 hours. The solvent was removed by evaporation and the residue partitioned between water (80 ml) and dichloromethane (2×100 ml). The organic layer was washed with saturated sodium chloride solution (50 ml) and dried (MgSO4). The solvent was removed by evaporation and the resultant yellow oil was purified by flash chromatography, eluting with increasing concentration of ethyl acetate in dichloromethane. The product was eluted with ethyl acetate/dichloromethane (10:90 v/v) to give 4-benzyloxy-5-chloro-2-ethylquinoline as a white solid (2.6 g), m.p. 78°-80° C.; NMR: 1.39(t,3H), 2.94(q,2H), 5.38(s,2H), 6.72(s,1 H), 7.30-7.55(m,6H), 8.0(d,1H), 8.13(d,1H).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue partitioned between water (80 ml) and dichloromethane (2×100 ml)
  3. washThe organic layer was washed with saturated sodium chloride solution (50 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed by evaporation
  6. customthe resultant yellow oil was purified by flash chromatography
  7. washeluting
  8. temperaturewith increasing concentration of ethyl acetate in dichloromethane
  9. washThe product was eluted with ethyl acetate/dichloromethane (10:90 v/v)

Sources & evidence

ORD record
ord-642b41ff9cb843e9ac165d2416eee68b
Source dataset
uspto-grants-1995_08
Patent number
US05444071

Reaction notes

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