Sodium Iodide → HCID 15168576, compound

HRID 484459Notes

Reaction equation

HRID 484459 reaction equation
Cl.[NH2:2][C@@H:3]1[C:12]2[C:7](=[CH:8][C:9]([Cl:14])=[CH:10][C:11]=2[Cl:13])[NH:6][C@@H:5]([C:15]([O:17]C)=[O:16])[CH2:4]1.C(N(CC)CC)C.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[I-].[Na+]>CN(C=O)C>[CH2:26]([NH:2][C@@H:3]1[C:12]2[C:7](=[CH:8][C:9]([Cl:14])=[CH:10][C:11]=2[Cl:13])[NH:6][C@@H:5]([C:15]([OH:17])=[O:16])[CH2:4]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 67690826HCID 67690826, compound

Product 1

HCID 15168576HCID 15168576, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of trans-4-amino-5,7-dichloro-2-methoxycarbonyl-1,2,3,4-tetrahydroquinoline hydrochloride (0.300 g, 0.96 mmol) in anhydrous DMF (10 ml) was added triethylamine (0.403 ml, 2.89 mmol), benzyl bromide (0.230 ml, 1.92 mmol) and a catalytic quantity of sodium iodide. This mixture was stirred under an atmosphere of nitrogen at room temperature for 90 hours. The solvent was removed in vacuo and the residue obtained was partitioned between distilled water (100 ml) and ethyl acetate (200 ml). The organic layer was washed with saturated sodium hydrogen carbonate (2×100 ml), brine (2×100 ml) and distilled water (2×100 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatrography on silica gel (using from 10% ethyl acetate in hexane to 50% ethyl acetate in hexane as eluents) to give the title compound as colourless crystals, m.p. 112°-114° C. δ (360 MHz, DMSO), 1.41 (1H, ddd, J=13.4, 12.3 and 3.1 Hz, CHACHBHCCHD), 2.33 (1H, dm, J=13.4 Hz, CHACHBHCCHD), 3.73 (3H, s, CO2CH3), 3.84 (2H, 2 d, J=13.5 Hz, CH2C6H ), 4.13 (1H, m, CHACHBHCCHD), 4.27 (1H, dd, J=12.3 and 2.8 Hz, CHACHBHCCHD), 6.60 (1H, d, J=2.1 Hz, 6-H or 8-H), 6.73 (1H, s, ArNH, 6.78 (1H, d, J=7.69 (1H, d, 2.1 Hz, 6-H or 8-H), 7.28 (3H, m, ArH), 7.37 (2H, m, ArH), 7.69 (1H, m, CHNHCH2); m/e (CI+) 365 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue obtained
  3. customwas partitioned
  4. distillationbetween distilled water (100 ml) and ethyl acetate (200 ml)
  5. washThe organic layer was washed with saturated sodium hydrogen carbonate (2×100 ml), brine (2×100 ml)
  6. distillationdistilled water (2×100 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatrography on silica gel (using from 10% ethyl acetate in hexane to 50% ethyl acetate in hexane as eluents)

Sources & evidence

ORD record
ord-5abd2a397b6844bc86cd8869e04c35e8
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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