Hydrochloric Acid → Hydrochloric Acid

HRID 1802349Notes

Reaction equation

HRID 1802349 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:6]#[N:7])[CH3:2].[ClH:13]>CO.[OH-].[OH-].[Pd+2]>[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH2:7])[CH3:2].[ClH:13]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 574847133-Ethyl-4-methoxybenzonitrile

Product 2

HCID 313Hydrochloric AcidHCID 227446271-(3-Ethyl-4-methoxyphenyl)methanamine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-ethyl-4-methoxybenzonitrile (6-2, 0.12 g, 0.71 mmol) in MeOH (3.5 mL) was added Pearlman's catalyst (0.020 g, 0.036 mmol, 20 weight percent) and concentrated HCl (0.47 mL, 5.71 mmol, 12 N). The system was then stirred under an atmosphere of hydrogen via a balloon overnight. The reaction contents were filtered through a pad of celite and solvents were removed in vacuo to yield the desired product (6-3) as a salmon colored crystalline solid in the form of a mono HCl salt. ESI+MS [M+H]+ C8H12N2O2: M-16 (—NH2), 149.07 found, 149.2 required.

Workup

  1. customThe reaction contents
  2. filtrationwere filtered through a pad of celite and solvents
  3. customwere removed in vacuo

Sources & evidence

ORD record
ord-7352290ce197432584b660497be89647
Source dataset
uspto-grants-2013_01
Patent number
US08349872B2

Reaction notes

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