Chlorosuccinimide → HCID 13930510, compound

HRID 1432867Notes

Reaction equation

HRID 1432867 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].[Cl:14]N1C(=O)CCC1=O>C(Cl)Cl.O>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([Cl:14])=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 639844Methyl indole-6-carboxylate

Product 1

HCID 13930510HCID 13930510, compoundYield 630.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1H-indole-6-carboxylic acid methyl ester (5.86 g, 33.5 mmol) in 30 mL of CH2Cl2 is added N-chlorosuccinimide (0.58, 4.33 mmol) portionwise over 1.5 hours. The mixture is stirred for 2 h, then diluted with water. The layers are separated and the organic phase is washed with water and saturated NaCl solution. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to give the title compound (5.74 g, 27.3 mmol). The crude product is used in the next step without further purification. 1H NMR (CDCl3, 300 MHz) δ8.46 (bs, 1H), 8.19 (s, 1H), 7.90 (dd, 1H), 7.69 (d, 1H), 7.36 (d, 1H), 3.97 (s, 3H).

Workup

  1. customThe layers are separated
  2. washthe organic phase is washed with water and saturated NaCl solution
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfe4f8f3838c4c789b560edfe0db7df9
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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