3-Aminobenzonitrile → HCID 9858039, compound

HRID 612100Notes

Reaction equation

HRID 612100 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].[NH2:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[C:21]#[N:22]>C(O)C>[C:21]([C:20]1[CH:19]=[C:18]([NH:17][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:25]=[CH:24][CH:23]=1)#[N:22]

Participants

4

Reactant 2

HCID 167023-AminobenzonitrileHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 9858039HCID 9858039, compoundYield 76%

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 3.04 g (25.8 mmol) 3-aminobenzonitrile was heated to reflux. Removed heat at 3.5 hours and made basic with saturated sodium bicarbonate. Stripped solvents and air dried. Slurried residue with hexane and collected solids. Washed with water and dried in vacuo. Boiled in large volume ethyl acetate, collected solids and dried in vacuo, giving 5.15 g of yellow-brown solid: mass spectrum (electrospray m/e): 316.0.

Workup

  1. temperaturewas heated to reflux
  2. customRemoved
  3. temperatureheat at 3.5 hours
  4. customdried
  5. customSlurried residue with hexane and collected solids
  6. washWashed with water
  7. customdried in vacuo
  8. customBoiled in large volume ethyl acetate, collected solids
  9. customdried in vacuo

Sources & evidence

ORD record
ord-3c17b95ddff24918aad260ea75e473b3
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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