Hydrochloric Acid → HCID 11156384, compound

HRID 557611Notes

Reaction equation

HRID 557611 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15](=[O:28])[C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[C:7]([C:30]2[CH:35]=[CH:34][C:33]([O:36]C)=[CH:32][CH:31]=2)([CH3:29])[CH2:6][C:5]1([CH3:39])[CH3:38])(=[O:3])[CH3:2].B(Br)(Br)Br.[OH-].[Na+].Cl>C(Cl)Cl.C(OCC)(=O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:15](=[O:28])[C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[C:7]([C:30]2[CH:31]=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=2)([CH3:29])[CH2:6][C:5]1([CH3:39])[CH3:38])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 17962890HCID 17962890, compound

Product 1

HCID 11156384HCID 11156384, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (0° C.) solution of 1-acetyl-4-(4-methoxyphenyl)-6-(4-phenylbenzoyl)amino-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline (0.46 g) in CH2Cl2 was added BBr3 under a nitrogen atmosphere. Complete conversion was reached after stirring for 3 h at room temperature. The mixture was cooled, 1 M NaOH was added until basic pH, subsequently ethyl acetate was added and the mixture was acidified with 1 M HCl. The organic layer was separated, dried (MgSO4) and concentrated. The residue was chromatographed on silicagel in heptane/ethyl acetate=1/0→0/1 (v/v) as eluent.

Workup

  1. temperatureThe mixture was cooled
  2. additionwas added
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silicagel in heptane/ethyl acetate=1/0→0/1 (v/v) as eluent

Sources & evidence

ORD record
ord-d4610e5892ed4af1b4ef5cf6af460c68
Source dataset
uspto-grants-2011_11
Patent number
US08058441B2

Reaction notes

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