Water → 2-Methylindoline

HRID 2119113Notes

Reaction equation

HRID 2119113 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.C([BH3-])#N.[Na+].O.[OH-].[Na+]>C(O)(=O)C>[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 72242-MethylindoleHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 233052-MethylindolineYield 92.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-methylindole (61.2 g) in acetic acid (525 g) at 15° C. was added sodium cyanoborohydride (81 g) in portions. The reaction was then drowned in ice and water (1500 g) and the aqueous solution neutralized with sodium hydroxide (350 g). The mixture was extracted with 3 portions of ether (300 ml). The ether fractions were water washed, dried, and evaporated to give 57.4 g of an oil which was identical with an authentic sample by IR and TLC.

Workup

  1. extractionThe mixture was extracted with 3 portions of ether (300 ml)
  2. washwashed
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-f85c6d5d26d34fc6a8ac2554ee0eba98
Source dataset
uspto-grants-1987_07
Patent number
US04683000

Reaction notes

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