Chlorosuccinimide → 3-chloro-1H-indole-5-carbaldehyde
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl:12]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:12][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[CH:5]=2)[NH:1][CH:2]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1H-indole-5-carbaldehyde (0.50 g, 3.44 mmol) in DCM (25 mL) was added N-chlorosuccinimide (0.44 g, 3.27 mmol). After 4 h, the mixture was washed with water (50 mL) and the organic layer was dried and concentrated to obtain the crude residue (0.62 g), which was used without purification. 1H NMR (CDCl3): 10.04 (s, 1H), 8.17-8.15 (m, 1H), 7.79 (dd, J=8.6, 1.5 Hz, 1H), 7.46 (d, J=8.6 Hz, 1), 7.29-7.28 (m,1H).
Workup
- washthe mixture was washed with water (50 mL)
- customthe organic layer was dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-be7f6b26d82e49818279e3a6257a59ee
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084466B2
Reaction notes
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