Sodium Bicarbonate → HCID 56640517, compound

HRID 1186724Notes

Reaction equation

HRID 1186724 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.ClCCl.C(=O)([O-])O.[Na+]>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 56640372HCID 56640372, compound

Product 1

HCID 56640517HCID 56640517, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an anhydrous dichloromethane (5 mL) suspension of 4-(3-methoxyphenyl)-1,4-dihydrobenzo[f]quinoxaline-2,3-dione (562 mg, 1.77 mmol) was added 1M boron tribromide/dichloromethane solution (2.12 mL, 2.12 mmol) under cooling in an ice-bath, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was poured into 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 an off-white crystal (280 mg, yield 52%).

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-33b976c91604405090030d9cb11c8b63
Source dataset
uspto-grants-2014_03
Patent number
US08673915B2

Reaction notes

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