Boron tribromide → HCID 21931653, compound

HRID 1244031Notes

Reaction equation

HRID 1244031 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:14])[N:10]2[CH3:13])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:14])[N:10]2[CH3:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21931803HCID 21931803, compound

Product 1

HCID 21931653HCID 21931653, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen, combined 1.3 g of 7-Methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one (6.8 mmol) with 18 ml of CH2Cl2. Added 15 ml of 1.0 M boron tribromide in CH2Cl2 (15.0 mmol) dropwise over 3 minutes. Stirred reaction for 5 hours, poured over ice-H2O, slurried for 15 minutes and filtered 818 mg of off-white solid (68%). 1H NMR (400 MHz, CD3OD) δ 2.56 (2H, t, J=7.88 Hz), 2.78 (2H, t, J=6.85 Hz), 3.29 (3H, s), 6.45 (1H, d, J=8.09 Hz), 6.54 (1H, d, J=2.07 Hz), 6.98 (1H, d, J=8.09 Hz). M/z (APCI+) 178.0 (M+1). HPLC (aqueous 200 mM ammonium acetate buffer/acetonitrile gradient, 3.0 ml/min, Hewlett Packard ODS Hypersil 5 uM, 125×4 mm column) 2.826.

Workup

  1. customreaction for 5 hours
  2. filtrationfiltered 818 mg of off-white solid (68%)

Sources & evidence

ORD record
ord-d32b9e9167e247328081ee521b7a4cf6
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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