3-azidomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one → 3-aminomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one

HRID 1887807Notes

Reaction equation

HRID 1887807 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][C:18]=2[Cl:23])[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:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[CH:6]=1

Participants

4

Reactant 1

HCID 712086763-azidomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one

Product 1

HCID 712085643-aminomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-oneYield 76.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a 100 mL round-bottom flask was added 3-azidomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one (215 mg, 0.623 mmol), ethyl acetate (20 mL) followed by platinum (IV) oxide (18.0 mg, 0.079 mmol). The reaction vessel was evacuated and back-filled with hydrogen gas via a balloon. Almost immediately the reddish color of the PtO2 turned black. The reaction mixture was stirred under a balloon of hydrogen gas at room temp overnight. The reaction mixture was filtered through a bed of celite. The filtrate was concentrated to give the crude 3-aminomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one (152 mg, 76.4%, 81% purity by HPLC). 1H NMR (DMSO-d6) δ ppm 8.23 (d, J=8.7 Hz, 1H) 7.80-7.92 (m, 2H) 7.59-7.79 (m, 3H) 7.41 (dd, J=8.7, 1.8 Hz, 1H) 6.66 (d, J=1.8 Hz, 1H) 3.58 (s, 2H) 1.69 (br. s., 2H). MS calcd. for C16H12Cl2N2O [(M+H)+] 320.0, obsd. 318.9, [(M-NH2)+] 303.0, obsd. 301.9.

Workup

  1. customThe reaction vessel was evacuated
  2. additionback-filled with hydrogen gas via a balloon
  3. filtrationThe reaction mixture was filtered through a bed of celite
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-eb4425cce7ca463d80562341cf112528
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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