3-Isopropylaniline → HCID 22466539, compound

HRID 1935151Notes

Reaction equation

HRID 1935151 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].[CH:17]([C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23])([CH3:19])[CH3:18]>C(O)C>[CH:17]([C:20]1[CH:21]=[C:22]([NH:23][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:24]=[CH:25][CH:26]=1)([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 4586793-IsopropylanilineHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 22466539HCID 22466539, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.00 g (21.5 mmol) 4-chloro-6-nitro-3-quinolinecarbonitrile, 200 ml ethanol, and 3.48 g (25.8 mmol) 3-isopropylaniline was heated to reflux under N2. At 4 hours, removed heat and made basic with saturated sodium bicarbonate. Stripped solvents and azeotroped with ethanol. Slurried residue with hexane and collected solids. Dissolved in ethyl acetate, stirred with Darco, filtered through celite, stripped solvent and dried in vacuo, giving 5.289 g of yellow solid: mass spectrum (electrospray m/e): M+H=333.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customremoved
  4. temperatureheat
  5. customazeotroped with ethanol
  6. customSlurried residue with hexane and collected solids
  7. dissolutionDissolved in ethyl acetate
  8. filtrationfiltered through celite
  9. customdried in vacuo

Sources & evidence

ORD record
ord-9a3bcb9127f348ffa4fb3f0665d77487
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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