6-Chloroindole → 6-Chloro-2,3-dihydro-1h-indole

HRID 751514Notes

Reaction equation

HRID 751514 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 871116-ChloroindoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 2585676-Chloro-2,3-dihydro-1h-indoleYield 117.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 6-chloro-1H-indole (2 g, 0.013 mol) in acetic acid (10 mL) under nitrogen. Add sodium cyanoborohydride (1.24 g, 1.5 eq) and stir 20 minutes at room temperature. Dilute with ethyl acetate and extract with sodium hydroxide (5 N aqueous). Dry over magnesium sulfate, filter and concentrate to give 2.35 g (116%) crude product. MS (ES, m/z): 154.0 (M+1).

Workup

  1. extractionextract with sodium hydroxide (5 N aqueous)
  2. dry with materialDry over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-be1641daf6684952910952a4da866c44
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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