Hydrochloric Acid → Hydrochloric Acid

HRID 1675964Notes

Reaction equation

HRID 1675964 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 (12-2, 0.12 g, 0.71 mmol) in MeOH (3.5 mL) was added Pearlman's catalyst (0.020 g, 0.036 mmol) and concentrated HCl (0.47 mL, 5.71 mmol). 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 (12-3) 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-873859b732cd419a8f3e30546d43f8eb
Source dataset
uspto-grants-2011_08
Patent number
US08003797B2

Reaction notes

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