Methanol → N-(8-Bromo-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamide

HRID 1643899Notes

Reaction equation

HRID 1643899 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][C@@H:7]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:6]2)#[N:2].CO.C([O-])([O-])=O.[Ca+2].[Br-:30].[Br-].[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C([N+](CC)(CC)CC)C1C=CC=CC=1.C([N+](CC)(CC)CC)C1C=CC=CC=1>C1COCC1.C(Cl)Cl>[Br:30][C:11]1[CH:12]=[C:3]([C:1]#[N:2])[CH:4]=[C:5]2[C:10]=1[NH:9][CH2:8][CH:7]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:6]2

Participants

7

Reactant 4

HCID 887MethanolHCID 10112Calcium CarbonateHCID 66757946(S)-N-(6-Cyano-1,2,3,4-tetrahydro-quinolin-3-yl)-benzenesulfonamideHCID 86596066Benzyltriethylammonium tribromide

Product 1

HCID 66757940N-(8-Bromo-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamideYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of racemate 1G (323 mg, 1.03 mmol) in mixed solvents of MeOH (3 mL), CH2Cl2 (3 mL) and THF (3 mL) at RT was added CaCO3 (103 mg, 1.03 mmol), followed by benzyltriethylammonium tribromide (445 mg, 1.03 mmol). After addition, the mixture was stirred at RT for 45 min. The resultant precipitate was collected by filtration, washed with 0.2 N aqueous HCl, H2O, then dried to provide the title compound (311 mg, 77%) as a white solid.

Workup

  1. additionAfter addition
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with 0.2 N aqueous HCl, H2O
  4. customdried

Sources & evidence

ORD record
ord-45e711c1f9c444a19d24daf9069beae8
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

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