1-Bromo-3-chloropropane → HCID 15481570, compound

HRID 1954178Notes

Reaction equation

HRID 1954178 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7](=[O:13])[C:6]([C:14]1[N:15]=[N:16][N:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][C:28]4[CH:37]=[CH:36][C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[N:29]=4)[CH:21]=3)[N:18]=1)=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:45][CH2:46][CH2:47][Cl:48]>CN(C=O)C>[Cl:48][CH2:47][CH2:46][CH2:45][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7](=[O:13])[C:6]([C:14]1[N:15]=[N:16][N:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][C:28]4[CH:37]=[CH:36][C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[N:29]=4)[CH:21]=3)[N:18]=1)=[CH:5]2

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 15481607HCID 15481607, compound

Product 1

HCID 15481570HCID 15481570, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 6-hydroxy-1-methyl-3-{2-[3-(2-quinolylmethoxy)benzyl]tetrazolyl}quinolin-2-one (600 mg, 1.22 mmol) and potassium carbonate (337 mg, 2.44 mmol), was added DMF (100 ml), and the resultant mixture was stirred. 1-Bromo-3-chloropropane (578 mg, 3.64 mmol) was then added thereto, followed by stirring at a bath temperature of 60° C. for four hours. The reaction mixture was concentrated under reduced pressure, and water was added thereto, followed by extraction with a mixture of chloroform-methanol (10:1). The residue was dried over sodium sulfate anhydrate, and the solvent was removed under reduced pressure, to thereby obtain the title compound (638 mg) in a crude form as yellow oily matter.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  2. additionwas added
  3. extractionfollowed by extraction with a mixture of chloroform-methanol (10:1)
  4. dry with materialThe residue was dried over sodium sulfate anhydrate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6b2c5dc477374d20bcda6637d6c6dc86
Source dataset
uspto-grants-2000_09
Patent number
US06121286

Reaction notes

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