Boron tribromide → HCID 21289298, compound

HRID 868148Notes

Reaction equation

HRID 868148 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13]C)[NH:9][CH:8]=[C:7]([C:15]([NH:17][N:18]1[CH2:22][CH2:21][NH:20][C:19]1=[O:23])=[O:16])[C:6]2=[O:24].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[NH:9][CH:8]=[C:7]([C:15]([NH:17][N:18]1[CH2:22][CH2:21][NH:20][C:19]1=[O:23])=[O:16])[C:6]2=[O:24]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 212892941,4-Dihydro-6,7-dimethoxy-4-oxo-N-(2-oxo-1-imidazolidinyl)-3-quinolinecarboxamide

Product 1

HCID 21289298HCID 21289298, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1,4-dihydro-6,7-dimethoxy-4-oxo-N-(2-oxo-1-imidazolidinyl)-3-quinolinecarboxamide (23.1 g, 69.5 mmol) in 1.2 l of dichloromethane, a solution of boron tribromide (104.5 g, 417 mmol) was added dropwise at 0° C. After stirring for 3 days at room temperature, the precipitate was filtered off, washed with dichloromethane and was then added to 300 ml of methanol under ice cooling. After stirring for 2 hours, the solid was filtered off, washed with methanol and dried in vacuo. Yield: 24.8 g (still contained some starting material). The reaction was repeated to give 18.4 g of the title compound after methanol treatment, melting point>300° C.

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with dichloromethane
  3. additionwas then added to 300 ml of methanol under ice cooling
  4. stirringAfter stirring for 2 hours
  5. filtrationthe solid was filtered off
  6. washwashed with methanol
  7. customdried in vacuo

Sources & evidence

ORD record
ord-c895a33739ce4256868be2666bbab102
Source dataset
uspto-grants-1988_10
Patent number
US04777252

Reaction notes

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