Sodium hydride → 3-amino-1-(2-methoxyethyl)-3,4-dihydroquinolin-2(1H)-one

HRID 1178442Notes

Reaction equation

HRID 1178442 reaction equation
[H-].[Na+].Cl.[NH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:15].[CH3:16][O:17][CH2:18][CH2:19]Br>CN(C=O)C.CCOC(C)=O>[NH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:19][CH2:18][O:17][CH3:16])[C:6]1=[O:15]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 134994283-Amino-3,4-dihydroquinolin-2(1H)-one--hydrogen chloride (1/1)

Product 1

HCID 219068373-amino-1-(2-methoxyethyl)-3,4-dihydroquinolin-2(1H)-oneYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% in oil, 321 mg, 8.03 mmol) was added to 3-amino-3,4-dihydroquinolin-2(1H)-one hydrochloride (J. Med. Chem., 28, 1985; 1511-16; 759 mg, 3.82 mmol) in anhydrous DMF (10 mL) at 0° C. over a period of 5 min. After 1 hour 2-bromoethyl methyl ether (0.40 mL, 4.20 mmol) was added and stirring maintained for 18 hours. The reaction was diluted with EtOAc (100 mL) and washed with sat. aqueous K2CO3 (20 mL). The aqueous was extracted with DCM (3×50 mL) and the combined organics dried (Na2SO4), filtered and evaporated. The residue was purified by column chromatography (DCM to DCM:MeOH (4:1)) to afford the title compound (654 mg, 78%) as a brown oil.

Workup

  1. temperaturemaintained for 18 hours
  2. washwashed with sat. aqueous K2CO3 (20 mL)
  3. extractionThe aqueous was extracted with DCM (3×50 mL)
  4. dry with materialthe combined organics dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (DCM to DCM:MeOH (4:1))

Sources & evidence

ORD record
ord-84fe54301f124347a9b405034d9752ad
Source dataset
uspto-grants-2007_10
Patent number
US07276517B2

Reaction notes

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