3-Aminobenzonitrile → HCID 9858039, compound

HRID 548438Notes

Reaction equation

HRID 548438 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-d24605ee5d654841aa156494b1045197
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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