Sodium Bicarbonate → HCID 10131458, compound

HRID 611991Notes

Reaction equation

HRID 611991 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]#[N:15])=[C:7]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)([O-])=O.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:14]#[N:15])=[C:7]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 9924935HCID 9924935, compound

Product 1

HCID 10131458HCID 10131458, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A slurry of 6.00 g(16.8 mmol) of 6-nitro-4-[(3-trifluoromethylphenyl)amino]-3-quinolinecarbonitrile and 18.9 g (83.3 mmol) of SnCl2 dihydrate in 240 mL of ethanol was refluxed under N2 for 1 h. After cooling to 25° C., the reaction was diluted with ice water, neutralized with sodium bicarbonate and stirred for 2 h. The product was extracted with chloroform, treated with Darco, dried(magnesium sulfate) and evaporated. The residue was filtered through silica gel(10% methanol in chloroform), evaporated and dried in vacuo(40° C.) to give 4.87 g of brown solid: mass spectrum (electrospray, m/e): M+H 329.

Workup

  1. extractionThe product was extracted with chloroform
  2. additiontreated with Darco, dried(magnesium sulfate)
  3. customevaporated
  4. filtrationThe residue was filtered through silica gel(10% methanol in chloroform)
  5. customevaporated
  6. customdried in vacuo(40° C.)

Sources & evidence

ORD record
ord-4fe06f283388494aacc9ca07c9995d71
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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