HCID 10223619, compound → HCID 10110652, compound

HRID 548421Notes

Reaction equation

HRID 548421 reaction equation
[I: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)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]([I:1])[CH:3]=1

Participants

3

Reactant 1

HCID 10223619HCID 10223619, compound

Product 1

HCID 10110652HCID 10110652, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.70 g (16.1 mmol) 4-[(3-iodophenyl)amino]-6-nitro-quinoline-3-carbonitrile, 300 ml ethanol, and 18.2 g (80.5 mmol) SnCl2 dihydrate was heated to reflux under N2. Removed heat at 2 hours, added ice water. Added sodium bicarbonate until pH was basic, forming a thick yellow mixture. Stirred for 2½ hours. Extracted with chloroform, stirred organic portion with Darco and filtered through magnesium sulfate. Stripped solvent and dried in vacuo, giving 3.48 g of yellow-brown solid: mass spectrum (electrospray m/e): M+H=387.0.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 2 hours
  5. additionadded ice water
  6. customforming a thick yellow mixture
  7. extractionExtracted with chloroform
  8. stirringstirred organic portion with Darco
  9. filtrationfiltered through magnesium sulfate
  10. customdried in vacuo

Sources & evidence

ORD record
ord-206392e0f5634d86847edba50b88ca8c
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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