Ammonium Chloride → (1-Tosyl-1H-indol-4-YL)methanamine

HRID 475184

Reaction equation

HRID 475184 reaction equation
[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:20]=[N:21]O)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[NH4+].[Cl-]>CCO.[Zn]>[S:1]([N:11]1[C:19]2[C:14](=[C:15]([CH2:20][NH2:21])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 866947201-tosyl-1H-indole-4-carbaldehyde oxime

Product 1

HCID 67262154(1-Tosyl-1H-indol-4-YL)methanamineYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

To a solution of 44 (620 mg, 2 mmol) in EtOH (15 mL) was added zinc powder (320 mg, 5.0 mmol) and NH4Cl (0.53 g, 10 mmol). The reaction mixture was heated at reflux overnight, filtered and the filtrate was concentrated to dryness. The residue was diluted with DCM (100 mL) and water (20 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated to afford 600 mg (100%) of (1-tosyl-1H-indol-4-yl)methanamine (46) as yellow syrup: MS (ESI) m/z=284.1 [M−15]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated to dryness
  5. additionThe residue was diluted with DCM (100 mL) and water (20 mL)
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2ed973f2124e4f32b3d4ad3f5aa61fe1
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Linked notes

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