Chloroform → Hydrochloric Acid

HRID 1823959Notes

Reaction equation

HRID 1823959 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])#[N:2].[H][H].C(Cl)(Cl)[Cl:16]>CCO.O=[Pt]=O>[NH2:2][CH2:1][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[ClH:16]

Participants

7

Reactant 3

HCID 6212ChloroformHCID 582554Methyl 2-cyanobenzoateHCID 178418361HCID 178418361, compound

Product 2

HCID 313Hydrochloric AcidHCID 2760944Methyl 2-(aminomethyl)benzoate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of methyl 2-cyanobenzoate (1.0 g, 6.2 mmol) and PtO2 (100 mg) in 20 mL EtOH and 1 ml of chloroform was hydrogenated under 50 psi of hydrogen for 2 h. The reaction mixture was filtered through Celite® in a sintered glass funnel and concentrated on a rotary evaporator to give methyl 2-(aminomethyl)benzoate as a HCl salt and this was carried to the next step crude.

Workup

  1. filtrationThe reaction mixture was filtered through Celite® in a sintered glass funnel
  2. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-10aab6ff56c340c5a19daf6a4cf52948
Source dataset
uspto-grants-2006_05
Patent number
US07041693B2

Reaction notes

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