Sodium Bicarbonate → 6-Amino-4-(3,4-dibromophenylamino)quinoline-3-carbonitrile

HRID 548413Notes

Reaction equation

HRID 548413 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:23]#[N:24])[CH:5]=[CH:6][C:7]=1[Br:8].C(=O)(O)[O-].[Na+]>C(O)C>[NH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][C:11]([C:23]#[N:24])=[C:10]2[NH:9][C:4]1[CH:5]=[CH:6][C:7]([Br:8])=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 101146524-[(3,4-Dibromophenyl)amino]-6-nitro-quinoline-3-carbonitrile

Product 1

HCID 101589666-Amino-4-(3,4-dibromophenylamino)quinoline-3-carbonitrileYield 27.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4.90 g (10.9 mmol) of 4-[(3,4-dibromophenyl)amino]-6-nitro-quinoline-3-carbonitrile and 12.4 g (54.7 mmol) of SnCl2 dihydrate in 200 mL of ethanol was refluxed under N2 for 1.5 h. After cooling to 25° C., the reaction was diluted with ice water, neutralized with sodium bicarbonate and stirred for 2 h. This solution was then extracted with chloroform, treated with Darco, dried (magnesium sulfate) and evaporated. After drying in vacuo (40° C.), there was obtained 1.25 g of brown solid: mass spectrum (electrospray, m/e): M+H 417, 419, 421.

Workup

  1. temperaturewas refluxed under N2 for 1.5 h
  2. extractionThis solution was then extracted with chloroform
  3. additiontreated with Darco
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated
  6. customAfter drying in vacuo (40° C.)

Sources & evidence

ORD record
ord-5e4b59ac929b48abba9036f720f56200
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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