Hydrochloric Acid → 7-(Methylthio)-3-nitroquinoline

HRID 1043780Notes

Reaction equation

HRID 1043780 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([NH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=O)[CH:6]=[CH:7][CH:8]=1.Cl.CSC1C=C(N)C=CC=1.C1(S)C=CC=CC=1>C(O)(=O)C>[CH3:1][S:2][C:3]1[CH:4]=[C:5]2[C:6]([CH:12]=[C:11]([N+:14]([O-:16])=[O:15])[CH:10]=[N:9]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 15693Benzenamine, 3-(methylthio)-HCID 72310184HCID 72310184, compound

Product 1

HCID 595074907-(Methylthio)-3-nitroquinolineYield 15.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a refluxing mixture of 3-[(3-methylthiophenyl)amino]-2-nitroprop-2-enal (2.3 g, 9.6 mmol) and the HCl salt of 3-methylthiophenylamine (2.7 g, 19.3 mmol) in acetic acid (25 mL) was added thiophenol (0.2 g, 1.9 mmol). After being refluxed for 18 h, the mixture was cooled to room temperature and the acetic acid was removed under reduced pressure. To the remaining dark colored solid EtOAc (50 mL) was added with stirring. Filtration gave a yellow/green solid and a dark filtrate. The product crystallized from the EtOAc solution upon standing. Filtration and rinsing with cold EtOAc gave 330 mg crystalline product. The yellow/green solid was washed with 3×250 mL portions of dichloromethane. The dichloromethane washes were concentrated to give an additional 150 mg of product (23%). LC/MS (m/z): 221.1 (MH+), Rt 2.54 minutes.

Workup

  1. temperatureAfter being refluxed for 18 h
  2. customthe acetic acid was removed under reduced pressure
  3. additionTo the remaining dark colored solid EtOAc (50 mL) was added
  4. filtrationFiltration
  5. customgave a yellow/green solid
  6. customThe product crystallized from the EtOAc solution
  7. filtrationFiltration
  8. washrinsing with cold EtOAc

Sources & evidence

ORD record
ord-69310b88ead343ba94b96489f5141166
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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