Dimethylformamide → HCID 118323980, compound

HRID 1778261Notes

Reaction equation

HRID 1778261 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[C:17]([Br:19])[CH:18]=2)[N:15]=[C:14]([OH:20])[CH:13]=[C:12]3[Br:21])=[CH:4][CH:3]=1.[CH3:29]N(C)C=O.C([O-])([O-])=O.[Cs+].[Cs+].CI>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[C:17]([Br:19])[CH:18]=2)[N:15]([CH3:29])[C:14](=[O:20])[CH:13]=[C:12]3[Br:21])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178515442HCID 178515442, compound

Product 1

HCID 118323980HCID 118323980, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Into a 25-mL round-bottom flask, was placed 6-[bis(4-chlorophenyl)methyl]-4,8-dibromoquinolin-2-ol (360 mg, 0.67 mmol, 1.00 equip), N,N-dimethylformamide (15 mL), Cs2CO3 (654 mg, 2.01 mmol, 3.00 equip), and CH3I (190 mg, 1.34 mmol, 2.00 equip). The resulting solution was stirred overnight at 80° C. The resulting solution was diluted with water (80 mL). The solids were collected by filtration to yield 6-[bis(4-chlorophenyl)methyl]-4,8-dibromo-1-methyl-1,2-dihydroquinolin-2-one as a yellow solid. LCMS (ES, m/z) 552 [M+H]+

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-02052f62b7a640e69a7d5ddf219b3f2d
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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