Dimethylformamide → HCID 118324142, compound

HRID 1778235Notes

Reaction equation

HRID 1778235 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH:13]=[C:12]3[Br:20])=[CH:4][CH:3]=1.CN(C)C=O.[H-].[Na+].Br[CH2:36][C:37]([NH2:39])=[O:38]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH2:36][C:37]([NH2:39])=[O:38])[C:14](=[O:19])[CH:13]=[C:12]3[Br:20])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 118323938HCID 118323938, compound

Product 1

HCID 118324142HCID 118324142, compound

Procedure

Into a 25-mL round-bottom flask, was placed 6-[bis(4-chlorophenyl)methyl]-4-bromo-1,2-dihydroquinolin-2-one (300 mg, 0.65 mmol, 1.00 equip), N,N-dimethylformamide (10 mg, 0.14 mmol, 0.21 equip) and sodium hydride (52.3 mg, 1.31 mmol, 2.00 equip, 60%). To the resulting mixture was then added 2-bromoacetamide (108 mg, 0.78 mmol, 1.20 equip). The resulting solution was stirred for 2 h at room temperature. The reaction was then quenched by the addition of water (200 mL). The resulting solution was extracted with ethyl acetate (3×100 mL) and the organic layers combined and dried over sodium sulfate. The solids were filtered out. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with DCM: MeOH (20:1) to yield 2-[6-[bis(4-chlorophenyl)methyl]-4-bromo-2-oxo-1,2-dihydroquinolin-1-yl]acetamide as a white solid. LCMS (ES, m/z) 517 [M+H]+

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of water (200 mL)
  3. extractionThe resulting solution was extracted with ethyl acetate (3×100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solids were filtered out
  6. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-bdf8b30a6e254ee7927e17c2acf426ff
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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