1-(7-chloro-2H-chromen-4-yl)methanamine hydrochloride → 1-(7-chloro-3,4-dihydro-2H-chromen-4-yl)methanamine, hydrochloride

HRID 63078Notes

Reaction equation

HRID 63078 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH2:13][NH2:14])=[CH:8][CH2:9][O:10]2)=[CH:5][CH:4]=1>[Ni].CO.CC(O)=O>[ClH:2].[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([CH2:13][NH2:14])[CH2:8][CH2:9][O:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 902366481-(7-chloro-2H-chromen-4-yl)methanamine hydrochloride

Product 1

HCID 678571841-(7-chloro-3,4-dihydro-2H-chromen-4-yl)methanamine, hydrochlorideYield 92%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

Hydrogenation of 1-(7-chloro-2H-chromen-4-yl)methanamine hydrochloride (500 mg, 2.6 mmol) was carried out in the presence of Raney Nickel (300 mg) in 2:1 MeOH/HOAc under 50 psi of H2 for 16 h at 30° C. The reaction was filtered through Celite and concentrated in vacuo. Precipitation from EtOAc and filtration gave 280 mg (56%) of the title compound as a white solid. [M+H] calc'd for C10H12ClNO, 198. found 198.

Workup

  1. filtrationThe reaction was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customPrecipitation
  4. filtrationfrom EtOAc and filtration

Sources & evidence

ORD record
ord-df886aa037414ca0af6d222c5cbd48d9
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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