2-Bromopropane → HCID 66911305, compound

HRID 44175

Reaction equation

HRID 44175 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[CH3:13][C:14]([O-])(C)[CH3:15].[K+].C(Br)(C)C>CN(C=O)C.Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:14]([CH3:15])[CH3:13])[C:7](=[O:12])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 66911305HCID 66911305, compoundYield 38.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6-bromo-3,4-dihydro-1H-quinolin-2-one (750 mg, 3.32 mmol) in 20 ml dry DMF was added potassium tert-butylate (804 mg, 6.64 mmol). After the mixture was stirred for 30 min at room temperature, a solution of isopropyl bromide (814 mg, 6.64 mmol) in 10 ml dry DMF was added and the mixture heated to 80° C. After stirring for additional 48 h, the mixture was cooled to room temperature and diluted with 150 ml 1 N HCl. Extraction with ethyl acetate (2×100 mL) followed by washing of the organic extracts with water and brine, drying over MgSO4 and removal of the solvent in vacuo gave a light yellow solid. Purification by flash chromatography (hexanes/ethyl acetate, 4/1, Rf=0.21) gave 6-bromo-1-isopropyl-3,4-dihydro-1H-quinolin-2-one (347 mg, 1.29 mmol, 33%) as pale yellow solid.

Workup

  1. temperaturethe mixture heated to 80° C
  2. stirringAfter stirring for additional 48 h
  3. temperaturethe mixture was cooled to room temperature
  4. extractionExtraction with ethyl acetate (2×100 mL)
  5. washby washing of the organic extracts with water and brine
  6. dry with materialdrying over MgSO4 and removal of the solvent in vacuo
  7. customgave a light yellow solid
  8. customPurification by flash chromatography (hexanes/ethyl acetate, 4/1, Rf=0.21)

Sources & evidence

ORD record
ord-5ceeb796fc7647d8bdb01bfa4f4dd658
Source dataset
uspto-grants-2013_09
Patent number
US08541404B2

Linked notes

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