Ammonium Chloride → HCID 86689826, compound

HRID 2409016Notes

Reaction equation

HRID 2409016 reaction equation
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH:20]=[N:21]O)[CH:19]=[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].[Cl-].[NH4+]>CO.[Zn]>[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH2:20][NH2:21])[CH:19]=[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]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86689824HCID 86689824, compound

Product 1

HCID 86689826HCID 86689826, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde oxime (600 mg, 1.9 mmol) in MeOH (10 mL) was added zinc powder (600 mg, 9.5 mmol) and ammonium chloride (1.0 g, 19 mmol). The suspension was refluxed for 18 h and then the solid was filtered. The filtrate was diluted with DCM (200 mL) and water (50 mL). The organic layer was separated, dried (MgSO4), filtered, and concentrated to afford 503 mg (98%) of (1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanamine as yellow solid which was used in the next step without further purification; MS (ESI) m/z: 302.1 [M+1]

Workup

  1. temperatureThe suspension was refluxed for 18 h
  2. filtrationthe solid was filtered
  3. additionThe filtrate was diluted with DCM (200 mL) and water (50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dfeba36da9324dc59c9ecc123c37a46b
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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