Hydrochloric Acid → 3-aminomethyl-7-fluoro-1-(2-fluoro-phenyl)-1H-quinolin-4-one hydrochloride salt

HRID 1887813Notes

Reaction equation

HRID 1887813 reaction equation
[N:1]([CH2:4][C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([F:16])=[CH:11][CH:12]=2)[N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH:6]=1)=[N+]=[N-].Cl.[Cl:25]C(Cl)C.C(OCC)(=O)C>[Pt](=O)=O>[ClH:25].[NH2:1][CH2:4][C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([F:16])=[CH:11][CH:12]=2)[N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21873757Dichloroethane ethyl acetateHCID 712090683-azidomethyl-7-fluoro-1-(2-fluoro-phenyl)-1H-quinolin-4-one

Product 1

HCID 712088443-aminomethyl-7-fluoro-1-(2-fluoro-phenyl)-1H-quinolin-4-one hydrochloride saltYield 67%

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

In a 50 mL round bottom flask, 3-azidomethyl-7-fluoro-1-(2-fluoro-phenyl)-1H-quinolin-4-one (0.290 g, 0.929 mmol) was added platinum (IV) oxide (0.040 g, 0.176 mmol) and 4 N HCl (2 mL) in 1:1 dichloroethane-ethyl acetate (15 mL). The reaction was charged with 1 atm. H2 using a balloon and stirred at room temperature for 3 hr. The catalyst was filtered off and the filtrate evaporated to dryness to give 3-aminomethyl-7-fluoro-1-(2-fluoro-phenyl)-1H-quinolin-4-one hydrochloride salt (200 mg, 67% yield). The crude was used in subsequent steps without further purification.

Workup

  1. additionThe reaction was charged with 1 atm
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-70c78b02b93442e095801f88e07ef474
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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