Water → 5-methoxy-2,3-dihydro-1H-indole

HRID 1060624Notes

Reaction equation

HRID 1060624 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.C([BH3-])#N.[Na+].O.[OH-].[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 138725-MethoxyindoleHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 107019745-methoxy-2,3-dihydro-1H-indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Part A: To 5-methoxyindole (5.0 g) in glacial acetic acid (90 mL, 15-17° C.) was added sodium cyanoborohydride (6.41 g, 3 eq.), and the mixture was stirred 2 h. Water (250 mL) was added to the mixture, which was then cooled in an ice bath and made strongly basic with sodium hydroxide pellets. The solution was extracted with ether, which was then washed with water and brine and dried over MgSO4. The ether solution was concentrated to give 5-methoxyindoline, which was reacted without further purification.

Workup

  1. temperaturewas then cooled in an ice bath
  2. extractionThe solution was extracted with ether, which
  3. washwas then washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationThe ether solution was concentrated

Sources & evidence

ORD record
ord-18f0718edec9479d8b87410cb7a737c6
Source dataset
uspto-grants-2003_02
Patent number
US06525056B2

Reaction notes

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