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

HRID 2215832Notes

Reaction equation

HRID 2215832 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]=O)[CH:3]=[CH:2]1.Cl.[NH2:13]O.C([O-])(=O)C.[NH4+]>C(O)C.O.[Zn].[NH4+].[OH-]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:10][NH2:13])[CH:3]=[CH:2]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

To a solution of 1H-indole-7-carboxaldehyde (3.0 g, 20.68 mmol) in ethanol:H2O (3:1) (120 ml) was added hydroxylamine hydrochloride (2.87 g, 41.37 mmol) and ammonium acetate (4.78 g, 62.06 mmol). The reaction was stirred at room temperature for 2 h. To the reaction was added NH4OH (25 ml, 0.72 mmol) and zinc metal (11.0 g, 8.1 mmol) portion-wise. Upon completion, the reaction mixture was filtered, poured into ethyl acetate and washed with water. The organic layer was extracted with 1N HCl. The aqueous layer was then mad basic by the addition of 1N NaOH and extracted with ethyl acetate. The organic layer was washed with water, brine, dried (MgSO4), and concentrated to give a white solid that was dried under high vacuum overnight to give the title compound (2.69 g, 89%) which was used as is. 1H NMR (400 MHz, DMSO-d6) 11.0 (s, 1H), 7.38 (d, 1H, J=7.0 Hz), 7.29 (d, 1H, J=3.0 Hz), 7.0 (d, 1H, J=7.0 Hz), 6.92 (dd, 1H, J=7.0, <1 Hz), 6.4 (d, 1H, J=3.0 Hz), 3.97 (s, 2H). MS (electrospray, m/z) 147 (M++1), 145 (M−−1).

Workup

  1. filtrationUpon completion, the reaction mixture was filtered
  2. additionpoured into ethyl acetate
  3. washwashed with water
  4. extractionThe organic layer was extracted with 1N HCl
  5. additionmad basic by the addition of 1N NaOH
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water, brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customto give a white solid
  11. customthat was dried under high vacuum overnight

Sources & evidence

ORD record
ord-5855746e0e554861b152d1e40d8533db
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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