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

HRID 379108Notes

Reaction equation

HRID 379108 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:22]#[N:23])[CH:5]=[CH:6][CH:7]=1.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([C:22]#[N:23])=[C:9]2[NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 99292314-[(3-Bromophenyl)amino]-6-nitro-quinoline-3-carbonitrile

Product 1

HCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrileYield 106.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4.00 g (10.8 mmol) of 4-[(3-bromophenyl)amino]-6-nitro-quinoline-3-carbonitrile and 12.2 g (54.2 mmol) of SnCl2 dihydrate in 160 mL of ethanol was refluxed under N2 for 1.3 h. After cooling to 25° C., ice water and sodium bicarbonate were added and the mixture was stirred for 2 h. Extraction with chloroform, treatment with Darco, drying (magnesium sulfate) and solvent removal gave 3.9 g of brown crystals: mass spectrum (electrospray, m/e): M+H 339.

Workup

  1. temperaturewas refluxed under N2 for 1.3 h
  2. extractionExtraction with chloroform, treatment with Darco
  3. customdrying
  4. custom(magnesium sulfate) and solvent removal

Sources & evidence

ORD record
ord-d1bf573686c949829070d9e8a606618c
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

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