Sodium Hydroxide → HCID 19761429, compound

HRID 373838Notes

Reaction equation

HRID 373838 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.[BH3-]C#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 19761401HCID 19761401, compound

Product 1

HCID 19761429HCID 19761429, compoundYield 12.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1.8 g 2-(2-amino-5-methoxyphenyl)-1H-indole in 60 ml acetic acid at 15° was added 1.8 g NaCNBH3 and this mixture was stirred at room temperature overnight and thereafter poured into excess 50% NaOH in ice. Extraction with CH2Cl2, drying (MgSO4), concentration and flash chromatography using 1% EtOAc/CH2Cl2 as an eluent gave 0.23 g solid, m.p. 120°-123° C.

Workup

  1. extractionExtraction with CH2Cl2
  2. customdrying
  3. concentration(MgSO4), concentration and flash chromatography

Sources & evidence

ORD record
ord-ef58e72d46da4dd4b8f8bb2fb6b13dac
Source dataset
uspto-grants-1992_11
Patent number
US05166170

Reaction notes

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