Methanol → 2-Bromomethyl-8-methoxy-2,3-dihydro-furo[3,2-c]quinoline

HRID 633825Notes

Reaction equation

HRID 633825 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:21]=1[OH:22])=[CH:19][C:18]([O:23][CH3:24])=[CH:17][CH:16]=2)[CH:10]=[CH2:11].CO>ClCCl>[Br:1][CH2:11][CH:10]1[O:22][C:21]2[C:20]3[CH:19]=[C:18]([O:23][CH3:24])[CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[CH2:9]1

Participants

5

Reactant 3

HCID 887MethanolHCID 67184N-bromobutanimideHCID 178439550HCID 178439550, compound

Product 1

HCID 867307082-Bromomethyl-8-methoxy-2,3-dihydro-furo[3,2-c]quinolineYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
10 °C

Procedure

N-Bromosuccinimide (1.19 g, 6.69 mmol, 1.2 eq) is added at 10° C. to a stirred solution of 3-allyl-6-methoxy-quinolin-4-ol (1.20 g, 5.57 mmol, 1.0 eq) in dichloromethane (120 mL) and the resulting mixture is stirred at 10° C. for 1 hour. The reaction mixture is then successively washed with water (50 mL) and brine (20 mL), dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 80:1, v/v) to afford 2-bromomethyl-8-methoxy-2,3-dihydro-furo[3,2-c]quinoline as a light yellow solid (1.2 g, 73% yield).

Workup

  1. washThe reaction mixture is then successively washed with water (50 mL) and brine (20 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude product that
  6. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-45ece5120486491ca591308a4fcc341e
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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