Sodium Bicarbonate → HCID 86690017, compound

HRID 1186744Notes

Reaction equation

HRID 1186744 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:18]3[CH:17]=[CH:16][C:15]4[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=4[C:13]=3[NH:12][C:11](=[O:23])[C:10]2=[O:24])=[CH:5][CH:4]=1.B(Br)(Br)Br.ClCCl.C(=O)([O-])O.[Na+]>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:18]3[CH:17]=[CH:16][C:15]4[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=4[C:13]=3[NH:12][C:11](=[O:23])[C:10]2=[O:24])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 86690015HCID 86690015, compound

Product 1

HCID 86690017HCID 86690017, compoundYield 148.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an anhydrous dichloromethane (8 mL) suspension of 4-(4-methoxyphenyl)-1,4-dihydrobenzo[f]quinoxaline-2,3-dione (200 mg, 0.63 mmol) was added a 1M boron tribromide/dichloromethane solution (0.94 mL, 0.94 mmol) under cooling in an ice-bath. The mixture was stirred at room temperature for 18 hours. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution. The precipitated solid was washed with water and ethanol. The solid was further washed with hexane, and dried to obtain the titled compound as a off-white crystal (285 mg, yield 45%).

Workup

  1. temperatureunder cooling in an ice-bath
  2. washThe precipitated solid was washed with water and ethanol
  3. washThe solid was further washed with hexane
  4. customdried

Sources & evidence

ORD record
ord-8c369e7c5d6947058a7dc6e36351476f
Source dataset
uspto-grants-2014_03
Patent number
US08673915B2

Reaction notes

Loading…