Sodium Azide → 7-Azido-4-(5-methoxy-2-methylanilino)-6-nitro-3-quinolinecarbonitrile

HRID 2213730Notes

Reaction equation

HRID 2213730 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=3[CH3:23])=[C:7]([C:12]#[N:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25].[N-:27]=[N+:28]=[N-:29].[Na+]>>[N:27]([C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=3[CH3:23])=[C:7]([C:12]#[N:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25])=[N+:28]=[N-:29]

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 219563857-Chloro-4-(5-methoxy-2-methylanilino)-6-nitro-3-quinolinecarbonitrile

Product 1

HCID 219564947-Azido-4-(5-methoxy-2-methylanilino)-6-nitro-3-quinolinecarbonitrileYield 91.1%

Conditions

Temperature
60 °C

Procedure

A mixture of 0.7 g (1.9 mmol) of 7-chloro-4-(5-methoxy-2-methylanilino)-6-nitro-3-quinolinecarbonitrile and 0.62 g (9.5 mmol) of sodium azide is heated at 60° C. under nitrogen for 24 hours. The mixture is cooled and poured onto ice. The solid is collected by filtration, washed with water and dried to yield 0.65 g of 7-azido-4-(5-methoxy-2-methylanilino)-6-nitro-3-quinolinecarbonitrile as a yellow solid.

Workup

  1. temperatureThe mixture is cooled
  2. additionpoured onto ice
  3. filtrationThe solid is collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-3168478077de49b189d50548c4623d21
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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