Sodium hydride → Methyl (3-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate
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].Br[CH2:17][C:18]([O:20][CH3:21])=[O:19]>CN(C=O)C>[NH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:6]1=[O:15]Participants
Procedure
Sodium hydride (60% in oil, 2.52 g, 63.0 mmol) was added to 3-amino-3,4-dihydroquinolin-2(1 h)-one hydrochloride (J. Med. Chem. 28, 1985, 1511–16; 5.0 g, 25.2 mmol), in anhydrous DMF (100 mL) at 0° C. over a period of 5 min keeping the internal temperature at <10° C. The reaction was stirred for a further 30 min before addition of methyl bromoacetate (2.85 mL, 30.2 mmol), then stirred for a further 60 min. The reaction was quenched by addition of 1M aqueous HCl (5 mL) and the volatiles were removed by evaporation. The residue was dissolved in DCM (250 mL) and washed with sat. aqueous NaHCO3 (100 mL) and the organic layer was dried (MgSO4), filtered and evaporated to yield the title compound (5.89 g, 100%) as yellow paste which was used in the next reaction without further purification.
Workup
- customat <10° C
- customThe reaction was quenched by addition of 1M aqueous HCl (5 mL)
- customthe volatiles were removed by evaporation
- dissolutionThe residue was dissolved in DCM (250 mL)
- washwashed with sat. aqueous NaHCO3 (100 mL)
- dry with materialthe organic layer was dried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-62ab67f73d73492a8bc3f05d48f75419
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07169927B2
Reaction notes
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