Chlorosuccinimide → Methyl 2-chloro-1H-indole-3-carboxylate

HRID 1458623Notes

Reaction equation

HRID 1458623 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1.[Cl:14]N1C(=O)CCC1=O.Cl.CCOCC>C(Cl)(Cl)Cl>[Cl:14][C:2]1[NH:1][C:9]2[C:4]([C:3]=1[C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 589098Methyl indole-3-carboxylateHCID 10953452Ether hydrochloride

Product 1

HCID 19599424Methyl 2-chloro-1H-indole-3-carboxylateYield 48%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred suspension of methyl indole-3-carboxylate (6.0 g, 0.034 mole) in chloroform (200 ml) was treated with N-chlorosuccinimide (5.04 g, 0.038 mole) to afford a clear solution within 15 minutes. After 2 h at room temperature this was treated with 1M HCl/ether (34 ml, 0.034 mole) and allowed to stir for a further 1 h, then treated with excess 10% Na2 CO3 solution and the chloroform layer separated, dried (Na2 SO4) and concentrated in vacuo. The residual yellow solid was recrystallised from chloroform/60-80 petrol to afford the title compound (D 11a) as a beige solid (3.4 g, 48%).

Workup

  1. customto afford a clear solution within 15 minutes
  2. additiontreated with excess 10% Na2 CO3 solution
  3. customthe chloroform layer separated
  4. customdried (Na2 SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residual yellow solid was recrystallised from chloroform/60-80 petrol

Sources & evidence

ORD record
ord-9d383f2bc3ec40cbb70ed4c72389db33
Source dataset
uspto-grants-1998_12
Patent number
US05852014

Reaction notes

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