3-azidomethyl-7-chloro-1-phenyl-1H-quinolin-4-one → 3-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one

HRID 1887798Notes

Reaction equation

HRID 1887798 reaction equation
[N:1]([CH2:4][C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([Cl:16])=[CH:11][CH:12]=2)[N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=1)=[N+]=[N-]>[Pt](=O)=O.C(OCC)(=O)C>[NH2:1][CH2:4][C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([Cl:16])=[CH:11][CH:12]=2)[N:7]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:6]=1

Participants

4

Reactant 1

HCID 712080783-azidomethyl-7-chloro-1-phenyl-1H-quinolin-4-one

Product 1

HCID 712083983-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-oneYield 96.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a 250 mL round-bottomed flask was added 3-azidomethyl-7-chloro-1-phenyl-1H-quinolin-4-one (2.00 g, 6.44 mmol), ethyl acetate (120 mL) followed by platinum (IV) oxide (152 mg, 0.671 mmol). The reaction mixture was evacuated and back-filled with hydrogen gas using an atmospheric hydrogenation apparatus. The reaction mixture was stirred under hydrogen gas (1 atm.) at room temperature for 5 hr. TLC (40% ethyl acetate-hexanes) and LCMS indicated the absence of starting material. The reaction mixture was filtered through celite under N2 atmosphere, then the celite layer was washed with ethyl acetate. The combined filtrate and washings were concentrated to give 3-aminomethyl-7-chloro-1-phenyl-1H-quinolin-4-one (1.77 g, 96.6% crude yield) as a light beige/greyish solid. The material was used in the next step without further purification.

Workup

  1. customThe reaction mixture was evacuated
  2. additionback-filled with hydrogen gas
  3. filtrationThe reaction mixture was filtered through celite under N2 atmosphere
  4. washthe celite layer was washed with ethyl acetate
  5. concentrationThe combined filtrate and washings were concentrated

Sources & evidence

ORD record
ord-ab9e679b62d44165b789dfdedb5669ac
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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