3-Iodoaniline → HCID 10223619, compound

HRID 612068Notes

Reaction equation

HRID 612068 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=2)[N:13]=[CH:12][C:11]=1[C:23]#[N:24].C(=O)(O)[O-].[Na+]>C(O)C>[I:1][C:2]1[CH:3]=[C:4]([NH:5][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:23]#[N:24])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 122713-IodoanilineHCID 516892Sodium BicarbonateHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 10223619HCID 10223619, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.10 ml (25.7 mmol) 3-iodoaniline, 200 ml ethanol, and 5.00 g (21.4 mmol) 4-chloro-6-nitro-3-quinolinecarbonitrile was heated to reflux under N2 for 3.5 hours. Cooled and made basic with a saturated sodium bicarbonate. Stripped solvents and azeotroped with ethanol. Slurried residue with hexane and collected. Air dried, washed solids with water, and dried in vacuo. Dissolved solids in 400 ml ethyl acetate, stirred with Darco, filtered and removed solvent. Dried solids in vacuo to give 7.38 g of yellow solid: mass spectrum (electrospray m/e): M+H=417.0.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 3.5 hours
  3. temperatureCooled
  4. customazeotroped with ethanol
  5. customSlurried residue with hexane and collected
  6. customAir dried
  7. washwashed solids with water
  8. customdried in vacuo
  9. dissolutionDissolved solids in 400 ml ethyl acetate
  10. filtrationfiltered
  11. customremoved solvent
  12. customDried solids in vacuo

Sources & evidence

ORD record
ord-9342f51de7334616add6aeac6bb52cae
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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