Sodium Hydroxide → 6-Chloro-5-methyl-2,3-dihydro-1H-indole

HRID 356015Notes

Reaction equation

HRID 356015 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[CH3:11].C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][NH:8]2)=[CH:4][C:3]=1[CH3:11]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 107733546-chloro-5-methyl-1H-indole

Product 1

HCID 221860806-Chloro-5-methyl-2,3-dihydro-1H-indoleYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

6-Chloro-5-methylindole (D9) (0.109 g, 0.66 mmol) was stirred at 15° C. in glacial acetic acid (3 ml), and sodium cyanoborohydride (0.125 g, 1.98 mmol) was added. The mixture was stirred at 15° C. for 2 h, diluted with water (40 ml), basified with solid NaOH, and extracted with ether. The extract was dried (Na2SO4) and evaporated to give the title compound (0.105 g, 95%) as a light yellow solid.

Workup

  1. extractionextracted with ether
  2. dry with materialThe extract was dried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-98567b1f3638426da8000ac349344795
Source dataset
uspto-grants-1998_11
Patent number
US05834494

Reaction notes

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