Hydroxyamine hydrochloride → (1H-Indol-7-YL)methanamine

HRID 910115Notes

Reaction equation

HRID 910115 reaction equation
Cl.[NH2:2]O.C([O-])(=O)C.[NH4+].[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[CH:18]=O)[CH:11]=[CH:10]1>C(O)C.O.[Zn].[OH-].[NH4+]>[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[CH2:18][NH2:2])[CH:11]=[CH:10]1

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517165Ammonium AcetateHCID 2734629Indole-7-carboxaldehyde

Product 1

HCID 21950026(1H-Indol-7-YL)methanamineYield 89%

Reagents, catalysts & solvents 3

HCID 14923Ammonium HydroxideCatalystHCID 23994ZincCatalystHCID 19096565Water ethanolSolvent

Procedure

Add hydroxylamine hydrochloride (2.87 g, 41.37 mmol) and ammonium acetate (4.78 g, 62.06 mmol) to a solution of indole-7-carboxaldehyde (3.0 g, 20.68 mmol) in ethanol: H2O (3:1) (120 ml). Stir at room temperature for 2 hours. Add ammonium hydroxide (25 ml, 0.72 mmol) and zinc (11.0 g, 8.1 mmol) in portions. Filter the reaction mixture, dilute with ethyl acetate, and wash with water. Extract the organic layer with 1N HCl. Make the aqueous layer basic by adding 1N NaOH and extract with ethyl acetate. Wash the organic layer with water followed by saturated aqueous sodium chloride, dry over magnesium sulfate, and concentrate under reduced pressure to provide the desired compound (2.69 g, 89%) as a white solid.

Workup

  1. filtrationFilter the reaction mixture
  2. additiondilute with ethyl acetate
  3. washwash with water
  4. extractionExtract the organic layer with 1N HCl
  5. additionby adding 1N NaOH
  6. extractionextract with ethyl acetate
  7. washWash the organic layer with water
  8. dry with materialdry over magnesium sulfate
  9. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-9fae0dbc2cb240518c26b72effea50fb
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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