Water → HCID 67203620, compound

HRID 1472509Notes

Reaction equation

HRID 1472509 reaction equation
[CH:1]1[C:13]2[N:12]([C:14]3[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=[CH:16][CH:15]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:24]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:24][C:3]1[CH:2]=[CH:1][C:13]2[N:12]([C:14]3[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=[CH:16][CH:15]=3)[C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 67202850HCID 67202850, compound

Product 1

HCID 67203620HCID 67203620, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

62.5 g (207 mmol) of methyl 4-carbazol-9-ylnicotinate in 2000 ml of DMF are cooled to −10° C., 37.3 g (207 mmol) of N-bromosuccinimide are added in portions, and the mixture is stirred at room temperature for 6 h. 500 ml of water are subsequently added to the mixture, which is then extracted with CH2Cl2. The organic phase is dried over MgSO4, and the solvent is removed in vacuo. The product is washed by stirring with hot toluene and filtered off with suction. Yield: 71 g (186 mmol), 90% of theory, purity according to 1H-NMR about 98%.

Workup

  1. extractionis then extracted with CH2Cl2
  2. dry with materialThe organic phase is dried over MgSO4
  3. customthe solvent is removed in vacuo
  4. washThe product is washed
  5. stirringby stirring with hot toluene
  6. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-1d98c31ef19f4778936647ec1c5a7a6f
Source dataset
uspto-grants-2015_04
Patent number
US09012599B2

Reaction notes

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