Boron tribromide → HCID 131718775, compound

HRID 2379489Notes

Reaction equation

HRID 2379489 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[C:21]2[C:16](=[C:17]([CH3:23])[CH:18]=[C:19]([CH3:22])[CH:20]=2)[N:15]=[CH:14][C:13]=1[NH:24][C:25](=[O:38])[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34]C)[C:29]=1[O:36]C.C(=O)([O-])O.[Na+]>ClCCl>[OH2:34].[ClH:5].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[C:21]2[C:16](=[C:17]([CH3:23])[CH:18]=[C:19]([CH3:22])[CH:20]=2)[N:15]=[CH:14][C:13]=1[NH:24][C:25](=[O:38])[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[C:29]=1[OH:36]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 54347448HCID 54347448, compound

Product 1

HCID 131718775HCID 131718775, compoundYield 171.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide in dichloromethane (1:2, 2 ml) was dropwise added to a solution of 4-(2-chlorophenyl)-3-(2,3-dimethoxycinnamoylamino)-6,8-dimethylquinoline (0.94 g) in dichloromethane (15 ml) under ice-cooling and stirring. After being stirred for 30 minutes under ice-cooling, and further for 1.5 hours at room temperature, the mixture was poured into ice water. The solution was made neutral with a sodium hydrogen carbonate saturated solution and was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4). The solvent was removed, and the residue was dissolved into ethyl acetate (5 ml), to which 4N HCl-ethyl acetate solution (2 ml) was added to give crystals of 4-(2-chlorophenyl)-3-(2,3-dihydroxycinnamoylamino)-6,8-dimethylquinoline hydrochloric acid salt hydrate (0.85 g, 83.3%). The crystals were recrystallized from ethanol to obtain yellowish needles.

Workup

  1. temperaturecooling
  2. stirringAfter being stirred for 30 minutes under ice-
  3. temperaturecooling
  4. extractionwas extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed
  8. dissolutionthe residue was dissolved into ethyl acetate (5 ml), to which 4N HCl-ethyl acetate solution (2 ml)
  9. additionwas added

Sources & evidence

ORD record
ord-ff34d17d0caf44179bb2228b1d575c15
Source dataset
uspto-grants-1994_11
Patent number
US05362742

Reaction notes

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