Benzenamine, 3-ethynyl- → HCID 9836485, compound

HRID 379137Notes

Reaction equation

HRID 379137 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[C:17]([C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22])#[CH:18]>C(O)C>[C:17]([C:19]1[CH:20]=[C:21]([NH:22][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:23]=[CH:24][CH:25]=1)#[CH:18]

Participants

4

Reactant 2

HCID 104682Benzenamine, 3-ethynyl-HCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 9836485HCID 9836485, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.00 g (21.5 mmol) 4-chloro-6-nitro-quinoline-3-carbonitrile, 200 ml ethanol, and 3.82 g (32.6 mmol) 3-ethynylaniline was heated to reflux under N2. Removed heat at 3½ hours and added a solution of saturated sodium bicarbonate until basic. Stripped solvents and azeotroped with ethanol. Slurried residue with hexane and collected solids. Washed with water and dried in vacuo. Dissolved in ethyl acetate, stirred with Darco, filtered, stripped solvent and dried in vacuo, giving 4.544 g of yellow solid: mass spectrum (electrospray m/e): M+H=315.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 3½ hours
  5. additionadded a solution of saturated sodium bicarbonate until basic
  6. customStripped solvents and azeotroped with ethanol
  7. customcollected solids
  8. washWashed with water
  9. customdried in vacuo
  10. dissolutionDissolved in ethyl acetate
  11. filtrationfiltered
  12. customdried in vacuo

Sources & evidence

ORD record
ord-b33c1d0735e943548ae74c253f6dc49b
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

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