Water → HCID 22405251, compound

HRID 441245Notes

Reaction equation

HRID 441245 reaction equation
C[O:2][C:3]1[CH:29]=[CH:28][C:6]([C:7]([NH:9][C:10]2[CH:27]=[CH:26][C:13]([C:14]([N:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18][CH2:17]3)=[O:15])=[CH:12][CH:11]=2)=[O:8])=[C:5]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)[CH:4]=1.B(Br)(Br)Br.O>ClCCl>[OH:2][C:3]1[CH:29]=[CH:28][C:6]([C:7]([NH:9][C:10]2[CH:27]=[CH:26][C:13]([C:14]([N:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18][CH2:17]3)=[O:15])=[CH:12][CH:11]=2)=[O:8])=[C:5]([C:30]2[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 22405197HCID 22405197, compound

Product 1

HCID 22405251HCID 22405251, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-{4-[4-methoxy-2-(4-methylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline (380 mg) in dichloromethane (15 ml) at -78° C. was added a solution of 1.0M boron tribromide in dichloromethane (2.4 ml). The resulting solution was allowed to warm to ambient temperature where it was maintained for 12 hours. The mixture was cooled to 0° C., and added water. The organic layer was washed with saturated sodium bicarbonate aqueous solution and filtered through a bed of celite, and concentrated. The residue was triturated with diethyl ether to give 1-{4-[4-hydroxy-2-(4-methylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline (30 mg).

Workup

  1. temperaturewas maintained for 12 hours
  2. temperatureThe mixture was cooled to 0° C.
  3. washThe organic layer was washed with saturated sodium bicarbonate aqueous solution
  4. filtrationfiltered through a bed of celite
  5. concentrationconcentrated
  6. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-6ebfed48342e478a93e096237f2639b2
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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