Sodium hydride → HCID 43446516, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2].[H-].[Na+].[Cl:17][CH2:18][CH2:19][CH2:20]I>CN(C=O)C.O>[Cl:17][CH2:18][CH2:19][CH2:20][N:10]1[C:11]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][CH:12]=2)[CH2:7][CH2:8][C:9]1=[O:14]Participants
Procedure
To a stirred solution of 6-nitro-3,4-dihydroquinolin-2(1H)-one (5 g, 26.0 mmol) in DMF (100 ml), cooled to 0° C. was added sodium hydride (3.12 g, 78 mmol). The mixture was stirred until bubbling had ceased, then 1-chloro-3-iodopropane (8.23 ml, 78 mmol) was added. The reaction was kept in an ice bath and allowed to warm to room temperature slowly, then stirred overnight. The reaction mixture was then diluted with water and extracted with ethyl acetate (3×). The combined organics were then washed with a 1:1 mixture of brine and water (3×), then brine (1×). The organic phase was dried, filtered and concentrated then chromatographed in 10-50% ethyl acetate in hexanes, giving the desired 1-(3-chloropropyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (5.22 g, 19.43 mmol, 74.7% yield).
Workup
- customuntil bubbling
- customThe reaction was kept in an ice bath
- stirringstirred overnight
- extractionextracted with ethyl acetate (3×)
- washThe combined organics were then washed with a 1:1 mixture of brine and water (3×)
- customThe organic phase was dried
- filtrationfiltered
- concentrationconcentrated
- customthen chromatographed in 10-50% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-95c2a7bff85244c4a6bc37c666687576
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173813B2
Reaction notes
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