5-Chloro-2-methylindole → 5-chloro-2-methyl-2,3-dihydro-1H-indole

HRID 1172990Notes

Reaction equation

HRID 1172990 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[CH:5]2.C([BH3-])#N.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]([CH3:11])[CH2:5]2

Participants

5

Reactant 2

HCID 706365-Chloro-2-methylindoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 595568185-chloro-2-methyl-2,3-dihydro-1H-indoleYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-2-methylindole (1.00 g, 6.04 mmol) in acetic acid (7 ml) was added portionwise sodium cyanoborohydride (0.76 g, 12.1 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The resulting solution was diluted with ethyl acetate and washed sequentially with water and with 5 N aq. sodium hydroxide solution. The organic phase was dried over sodium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluant: heptane/ethyl acetate gradient) to yield the title compound as a colourless oil (1.00 g, 100%); MS (ISP): 170.2 ([{37Cl}M+H]+), 168.3 ([{35Cl}M+H]+).

Workup

  1. washwashed sequentially with water and with 5 N aq. sodium hydroxide solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (eluant: heptane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-3b885b7d0ce04970b0b4ef443d4d6706
Source dataset
uspto-grants-2010_11
Patent number
US07834044B2

Reaction notes

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