Boron tribromide → HCID 53794354, compound

HRID 2379488Notes

Reaction equation

HRID 2379488 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](C)[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][C:31]([O:34]C)=[C:30]([O:36]C)[CH:29]=1.[C:39](=O)([O-])O.[Na+]>ClCCl>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[C:21]2[C:16](=[CH:17][C:18]([CH3:39])=[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][C:31]([OH:34])=[C:30]([OH:36])[CH:29]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 54377199HCID 54377199, compound

Product 1

HCID 53794354HCID 53794354, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide in dichloromethane (1:2, 1 ml) was added to a solution of 4-(2-chlorophenyl)-3-(3,4-dimethoxycinnamoylamino)-6,8-dimethylquinoline (473 mg) in dichloromethane (5 ml) under ice-cooling. After being stirred for 20 minutes under ice-cooling, and further for 30 minutes 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 crystallized to give crystals of 4-(2-chlorophenyl)-3-(3,4-dihydroxycinnamoylamino)-6,7-dimethylquinoline (212 mg, 44.8%). The crystals were recrystallized from acetone to obtain yellowish prisms (1/2 acetone solvate).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. waitfurther for 30 minutes at room temperature
  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. customthe residue was crystallized

Sources & evidence

ORD record
ord-be932062a8a94e31b9240bdc4488f768
Source dataset
uspto-grants-1994_11
Patent number
US05362742

Reaction notes

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