Benzenamine, 3-(methylthio)- → 4-[(3-Methylsulfanylphenyl)amino]-6-nitro-3-quinolinecarbonitrile

HRID 1935158Notes

Reaction equation

HRID 1935158 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].[CH3:17][S:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22]>C(O)C>[CH3:17][S:18][C:19]1[CH:20]=[C:21]([NH:22][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:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 15693Benzenamine, 3-(methylthio)-HCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 224666284-[(3-Methylsulfanylphenyl)amino]-6-nitro-3-quinolinecarbonitrileYield 67%

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 3.18 ml (25.8 mmol) 3-methylsulfanylaniline was heated to reflux under N2. At 2 hours, removed heat and made basic with saturated sodium bicarbonate. Stripped solvents and air dried. Washed residue with hexane, collected solids and washed with water. Dissolved in ethyl acetate, stirred with Darco, stripped solvent and dried in vacuo, giving 4.848 g of yellow solid: mass spectrum (electrospray m/e): M+H=337.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customremoved
  4. temperatureheat
  5. customdried
  6. customWashed residue with hexane, collected solids
  7. washwashed with water
  8. dissolutionDissolved in ethyl acetate
  9. customdried in vacuo

Sources & evidence

ORD record
ord-eb1d44a174914f05b50986a7668b4834
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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