8-Bromo-5,6-difluoro-2,3-dihydrochromen-4-one oxime → 8-bromo-5,6-difluoro-3,4-dihydro-2H-chromen-4-amine

HRID 1363196Notes

Reaction equation

HRID 1363196 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:15])[C:5]([F:14])=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][C:7]2=[N:12]O>CO.[Ni]>[Br:1][C:2]1[CH:3]=[C:4]([F:15])[C:5]([F:14])=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH:7]2[NH2:12]

Participants

4

Reactant 1

HCID 866101588-Bromo-5,6-difluoro-2,3-dihydrochromen-4-one oxime

Product 1

HCID 669709088-bromo-5,6-difluoro-3,4-dihydro-2H-chromen-4-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney-Ni (5 mL slurry in water) was added to a solution of 8-bromo-5,6-difluoro-2,3-dihydrochromen-4-one oxime (1.9 g) in 200 mL MeOH. The mixture was hydrogenated at 50 psi for 24 hrs to provide 8-bromo-5,6-difluoro-3,4-dihydro-2H-chromen-4-amine. Pd/C (0.3 g) was added to the mixture and hydrogenation was resumed at 50 psi for 4 hours. The title compound was obtained after filtration and concentration in vacuo. 1H NMR (300 MHz, 10% CD3OD in CDCl3): δ 7.15 (q, 1H), 6.6 (m, 1H), 4.6 (bm, 1H), 4.25 (bm, 2H), 2.2-2.4 (m, 2H).

Sources & evidence

ORD record
ord-02e03a83641d4355a4982a04c67afe4d
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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