Sodium hydride → HCID 21906837, compound

HRID 1247525

Reaction equation

HRID 1247525 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 21906837HCID 21906837, compoundYield 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-8cdf941be0934c8e8835f9631b9965f6
Source dataset
uspto-grants-2006_10
Patent number
US07129249B2

Linked notes

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