3-Aminobenzonitrile → HCID 9858039, compound

HRID 379135Notes

Reaction equation

HRID 379135 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-quinoline-3-carbonitrile, 200 ml ethanol, and 3.04 g (25.8 mmol) 3-aminobenzonitrile was heated to reflux. Removed heat at 3½ 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 3½ 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-fe068ebdfb664a2cbf7a056b8c2e5fd8
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

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