Water → HCID 89601845, compound

HRID 526300Notes

Reaction equation

HRID 526300 reaction equation
[CH3:1][N:2]1[CH2:14][CH2:13][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[CH2:3]1.C1C(=O)N([Br:22])C(=O)C1.O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Br:22][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]2[CH2:1][N:2]([CH3:3])[CH2:14][CH2:13][C:5]=12

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 974242-methyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indoleHCID 516892Sodium Bicarbonate

Product 1

HCID 89601845HCID 89601845, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (3.7 g) in 40 mL of CHCl3 cooled at 0° C. was added 4 g of NBS in two portions. After stirring for 2 h at r.t., the reaction mixture was treated with 30 mL of water and 20 mL of saturated aqueous solution of NaHCO3, and then extracted with 200 mL of CH2Cl2. The extract was dried over Na2SO4 for 2 days, and then filtered through a pad of silica gel, concentrated to give 4 g of the title compound as a light brown solid.

Workup

  1. extractionextracted with 200 mL of CH2Cl2
  2. dry with materialThe extract was dried over Na2SO4 for 2 days
  3. filtrationfiltered through a pad of silica gel
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b31757ffe44b4694af66fd5bf6f6e248
Source dataset
uspto-grants-2016_05
Patent number
US09345905B2

Reaction notes

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