2,3-Dibromobutane → HCID 67171497, compound

HRID 551115Notes

Reaction equation

HRID 551115 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([CH:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]([OH:30])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.Br[CH:32]([CH:34](Br)[CH3:35])[CH3:33]>C(O)(C)C>[OH:30][C:9]1[C:10]([CH:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:2]([N:1]2[CH2:35][CH2:34][CH2:32][CH2:33]2)=[C:3]2[C:8]=1[N:7]=[CH:6][CH:5]=[CH:4]2

Participants

4

Reactant 2

HCID 215082,3-DibromobutaneHCID 67171864HCID 67171864, compound

Product 1

HCID 67171497HCID 67171497, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N-[(5-amino-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide (200 mg, 0.5 mmol), dibromobutane (0.1 ml), TEA (0.2 ml) in isopropanol were heated at reflux for 16 h. The reaction mixture was concentrated in vacuo, the residue dissolved in methylene chloride, washed with brine. The organic layer was dried over sodium sulfate and filtered. To the filtrate was added 1M HCl/ether, the solids filtered, washed with ether to give N-[(8-hydroxy-5-pyrrolidin-1-ylquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide as a purple solid.

Workup

  1. temperatureat reflux for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue dissolved in methylene chloride
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. additionTo the filtrate was added 1M HCl/ether
  8. filtrationthe solids filtered
  9. washwashed with ether

Sources & evidence

ORD record
ord-991e57e57f2646bb808f4e3c5d032f66
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

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