Hydrochloric Acid → 3-Aminomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide hydrochloride salt

HRID 1887794Notes

Reaction equation

HRID 1887794 reaction equation
[CH3:1][N:2]([CH3:27])[C:3]([C:5]1[N:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:7]2[C:12]([C:13](=[O:19])[C:14]=1[CH2:15][N:16]=[N+]=[N-])=[CH:11][CH:10]=[C:9]([Cl:20])[CH:8]=2)=[O:4].Cl>[Pt](=O)=O.C(Cl)Cl.C(OCC)(=O)C>[ClH:20].[CH3:1][N:2]([CH3:27])[C:3]([C:5]1[N:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:7]2[C:12]([C:13](=[O:19])[C:14]=1[CH2:15][NH2:16])=[CH:11][CH:10]=[C:9]([Cl:20])[CH:8]=2)=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 712090383-Azidomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide

Product 1

HCID 712087333-Aminomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide hydrochloride saltYield 147.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

In a 50 mL round-bottomed flask, 3-azidomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide (0.40 g, 1.05 mmol), platinum (IV) oxide (0.05 g, 0.204 mmol) and 4N HCl (0.1 mL) were added to 1:1 CH2Cl2/ethyl acetate (10 mL). The reaction was charged with 1 atm H2 using a balloon and stirred at room temperature for 4 hr. The catalyst was filtered off and washed with methanol. The filtrate was evaporated to afford 3-aminomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide hydrochloride salt (0.303 g, 74% yield). The intermediate was used in the next step without further purification. MS calcd. for C19H18ClN3O2 [(M+H)+] 356, obsd 356.

Workup

  1. additionThe reaction was charged with 1 atm H2 using a balloon
  2. filtrationThe catalyst was filtered off
  3. washwashed with methanol
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-4d2d44650b2f4021841ccf5a7b6467c5
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

Loading…