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

HRID 612262Notes

Reaction equation

HRID 612262 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+]>CCO>[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-nitroquinoline-3-carbonitrile and 8.00 g (31.9 mmol) of 3,4-dibromoaniline in 160 mL of EtOH was refluxed under N2 for 5 hr. Satd NaHCO3 was added and volatile material was removed. The residue was slurried with hexane, collected, washed with hexane and H2O and dried. The insoluble material was repeatedly extracted with boiling EtOAc and the solution was then filtered through silica gel. The solvent was removed to give 3.80 g of 4-(3,4-dibromophenylamino)-6-nitroquinoline-3-carbonitrile as a green solid: mass spectrum (electrospray, m/e): M+H 448.9.

Workup

  1. temperaturewas refluxed under N2 for 5 hr
  2. customvolatile material was removed
  3. customcollected
  4. washwashed with hexane and H2O
  5. customdried
  6. extractionThe insoluble material was repeatedly extracted with boiling EtOAc
  7. filtrationthe solution was then filtered through silica gel
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-bbc4c360a2594a26ad6379e1c4b0f366
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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