HCID 9836485, compound → HCID 9878925, compound

HRID 1935019Notes

Reaction equation

HRID 1935019 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-3-quinoline-carbonitrile, 100 ml ethanol, and 7.19 g (31.8 mmol) SnCl2 dihydrate was heated to reflux under N2. Removed heat at 3.5 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 3.5 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-2f73b19d631045a49f1ca2e31f59339c
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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