Sodium Azide → 3-Azidomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester

HRID 1887817

Reaction equation

HRID 1887817 reaction equation
Br[CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]=1[C:21]([O:23][CH3:24])=[O:22].[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[CH3:24][O:23][C:21]([C:4]1[N:5]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:6]2[C:11]([C:12](=[O:13])[C:3]=1[CH2:2][N:25]=[N+:26]=[N-:27])=[CH:10][CH:9]=[C:8]([Cl:14])[CH:7]=2)=[O:22]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86672058Methyl 3-(bromomethyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylate

Product 1

HCID 712088133-Azidomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 250 mL round-bottomed flask, methyl 3-(bromomethyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylate (2.7 g, 6.64 mmol) and sodium azide (1.25 g, 19.2 mmol) were combined with DMF (40 mL). The reaction mixture was stirred at room temperature overnight, then it was concentrated and triturated in ethyl acetate. The product 3-azidomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (2.3 g, 94%) was obtained as a white solid.

Workup

  1. concentrationit was concentrated
  2. customtriturated in ethyl acetate

Sources & evidence

ORD record
ord-acf3a7293e4e4c8b9bc2d26b46ada740
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Linked notes

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