Hydrogen Peroxide → HCID 67305047, compound

HRID 1009141Notes

Reaction equation

HRID 1009141 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:13])([CH3:12])[CH:6]=[CH:5]2.[O:14]1CCCC1.[OH-].[Na+].OO>CCOC(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:13])([CH3:12])[CH2:6][CH:5]2[OH:14]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 157119676-bromo-2,2-dimethyl-1H-quinoline

Product 1

HCID 67305047HCID 67305047, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-bromo-2,2-dimethyl-1,2-dihydroquinoline (4.50 g, 18.9 mmol) in tetrahydrofuran (37.8 ml, 18.9 mmol) was added BH3DMS (3.58 ml, 37.8 mmol) dropwise at 0 deg C. The resulting solution was allowed to warm to RT and stirred for 1 hour. The temperature was returned to 0 deg C. and sodium hydroxide (6N) (30.0 ml, 18.9 mmol) followed by Hydrogen peroxide (30.0 ml, 18.9 mmol) was slowly added to the reaction mixture. The resulting solution was stirred for 45 minutes and then transferred to a sep. funnel containing water and EtOAc. The layer were separated and the aqueous layer was subsequently washed 3× with DCM. The organic layers were dried with MgSO4, filtered and concentrated. The crude mixture was then purified with the MPLC (100% DCM to 10% 90:10:1 DCM:MeOH:NH4OH) to provide the desired product. MS m/z: 257 (M+1).

Workup

  1. customwas returned to 0 deg C
  2. additionwas slowly added to the reaction mixture
  3. stirringThe resulting solution was stirred for 45 minutes
  4. customThe layer were separated
  5. washthe aqueous layer was subsequently washed 3× with DCM
  6. dry with materialThe organic layers were dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude mixture was then purified with the MPLC (100% DCM to 10% 90:10:1 DCM:MeOH:NH4OH)

Sources & evidence

ORD record
ord-f80a4c8cd35943b09f11a08ec9169bd7
Source dataset
uspto-grants-2011_07
Patent number
US07973047B2

Reaction notes

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