Methanol → 3-bromo-6,7-dihydro-8(5H)-Quinolinone

HRID 1526632Notes

Reaction equation

HRID 1526632 reaction equation
C(=[C:8]1/[CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([Br:18])[CH:15]=[N:16][C:17]/1=2)/C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[OH:39]>C(Cl)Cl>[Br:18][C:14]1[CH:15]=[N:16][C:17]2[C:8](=[O:39])[CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11776TriphenylphosphineHCID 90415789HCID 90415789, compound

Product 1

HCID 597071133-bromo-6,7-dihydro-8(5H)-QuinolinoneYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-8-benzylidene-3-bromo-5,6,7,8-tetrahydroquinoline (0.82 g, 2.5:1 mixture with benzaldehyde) in MeOH (40 mL) and DCM (40 mL) was cooled to −78° C. and ozone was bubbled through the solution for 5 min until the solution turned light blue. Oxygen was passed through the solution for 10 min until the solution turned colorless and triphenylphosphine (1.03 g, 3.93 mmol) was added. The solution was removed from the dry ice/acetone bath and allowed to warm to RT. The reaction mixture was stirred at RT for 1 h. The reaction mixture was concentrated. Purification by flash column chromatography on silica gel eluting with 30% to 70% EtOAc in heptane) gave 3-bromo-6,7-dihydroquinolin-8(5H)-one (0.460 g, 2.04 mmol, 75% yield) as a white solid. LC/MS (ESI+) m/z=225.9 (M+H). Calculated for C9H8BrNO 225.0.

Workup

  1. customozone was bubbled through the solution for 5 min until the solution
  2. customThe solution was removed from the dry ice/acetone bath
  3. concentrationThe reaction mixture was concentrated
  4. customPurification by flash column chromatography on silica gel eluting with 30% to 70% EtOAc in heptane)

Sources & evidence

ORD record
ord-8a633857ee814561930e94992c4a7038
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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