Water → 2-Methylindoline

HRID 622597Notes

Reaction equation

HRID 622597 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-6a33482211de4034b62e90f41e3476fd
Source dataset
uspto-grants-1988_09
Patent number
US04772313

Reaction notes

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