Sodium Bicarbonate → 4-[(3,4-Dibromophenyl)amino]-6-nitro-quinoline-3-carbonitrile

HRID 611987

Reaction equation

HRID 611987 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[Br:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[Br:25])[NH2:21].C(=O)(O)[O-].[Na+]>C(O)C>[Br:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:22]=[CH:23][C:24]=1[Br:25]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5219813,4-DibromoanilineHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 101146524-[(3,4-Dibromophenyl)amino]-6-nitro-quinoline-3-carbonitrileYield 31.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.20 g (26.6 mmol)of 4-chloro-6-nitro-3-quinolinecarbonitrile and 8.00 g (31.9 mmol) of 3,4-dibromoaniline in 160 mL of ethanol was refluxed under N2 for 5 h. Saturated sodium bicarbonate was added and volatile material was removed. The residue was slurried with hexane, collected, washed with hexane and water and dried. The insoluble material was repeatedly extracted with boiling ethyl acetate and the solution was then filtered through silica gel. The solvent was removed to give 3.80 g of green solid: mass spectrum (electrospray, m/e): M+H 449.

Workup

  1. temperaturewas refluxed under N2 for 5 h
  2. customvolatile material was removed
  3. customcollected
  4. washwashed with hexane and water
  5. customdried
  6. extractionThe insoluble material was repeatedly extracted with boiling ethyl acetate
  7. filtrationthe solution was then filtered through silica gel
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-dfd6f5ececb44d5498cd67dc6b72efc5
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Linked notes

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