Dichloromethane → HCID 178479625, compound

HRID 1386386Notes

Reaction equation

HRID 1386386 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].Br.Br[CH2:21][CH2:22][C:23]1[N:24]=[CH:25][NH:26][CH:27]=1.C(Cl)[Cl:29]>C(C#N)(C)=O.CN(C=O)C>[ClH:29].[NH:26]1[CH:27]=[C:23]([CH2:22][CH2:21][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)[N:24]=[CH:25]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenoneHCID 178419249HCID 178419249, compound

Product 1

HCID 178479625HCID 178479625, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 694302-OxopropiononitrileSolvent2×

Procedure

6-Hydroxytetralone (1.46 g, 9.01 mmol) was dissolved in a mixture of 15 mL AcCN and 8 mL DMF, and solid potassium carbonate (4.98 g, 36 mmol) was added followed by a solution of 4-(2-bromoethyl)-1H-imidazole hydrobromide (2.05 g, 8.01 mmol) in a mixture of 15 mL AcCN and 3 mL DMF. After stirring for 24 hours at room temperature, the reaction was concentrated in vacuo to remove the solvents, and the resulting residue vias diluted with water and extracted into EtOAc. The pooled organics were washed sequentially with a saturated solution of NaHCO3, water, and brine and concentrated in vacuo to afford 1.57 g of crude product. Purification by flash chromatography (silica gel, 235 g, 5% MeOH in DCM) gave a yellow oil. The oil was taken up in 7 mL DCM, and the product was precipitated as a salt by the addition of 1.5 mL of 8N HCl in iPrOH. The solid was collected, washed with iPrOH, triterated with Et2O, and dried in vacuo to afford 0.826 g (33%) of the title compound;

Workup

  1. additionwas added
  2. concentrationthe reaction was concentrated in vacuo
  3. customto remove the solvents
  4. additionthe resulting residue vias diluted with water
  5. extractionextracted into EtOAc
  6. washThe pooled organics were washed sequentially with a saturated solution of NaHCO3, water, and brine
  7. concentrationconcentrated in vacuo
  8. customto afford 1.57 g of crude product
  9. customPurification by flash chromatography (silica gel, 235 g, 5% MeOH in DCM)
  10. customgave a yellow oil
  11. customthe product was precipitated as a salt by the addition of 1.5 mL of 8N HCl in iPrOH
  12. customThe solid was collected
  13. washwashed with iPrOH
  14. customdried in vacuo

Sources & evidence

ORD record
ord-352af1501bf746eca8d45001ec0241c0
Source dataset
uspto-grants-2001_07
Patent number
US06265422B1

Reaction notes

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