HCID 9836485, compound → HCID 9878925, compound

HRID 548439Notes

Reaction equation

HRID 548439 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1)#[CH:2]>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:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[CH:2])[CH:4]=1

Participants

3

Reactant 1

HCID 9836485HCID 9836485, compound

Product 1

HCID 9878925HCID 9878925, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.00 g (6.36 mmol) 4-[(3-ethynylphenyl)amino]-6-nitro-quinoline-3-carbonitrile, 100 ml ethanol, and 7.19 g (31.8 mmol) SnCl2 dihydrate was heated to reflux under N2. Removed heat at 3½ hours and added ice water. Made basic with sodium bicarbonate and stirred for 2 hours. Extracted with chloroform, stirred organic layer with Darco, dried with sodium sulfate, filtered, stripped solvent, and dried in vacuo, giving 1.737 g of yellow-brown solid: mass spectrum (electrospray m/e): M+H=285.2.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 3½ hours
  5. additionadded ice water
  6. extractionExtracted with chloroform
  7. stirringstirred organic layer with Darco
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. customdried in vacuo

Sources & evidence

ORD record
ord-2a718f321b74402c9ac32c5249ea01c9
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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