Hydrochloric Acid → HCID 178488024, compound

HRID 859982Notes

Reaction equation

HRID 859982 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([OH:13])[C:7](O)=[CH:6]2.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[Cl:23])[NH2:19].CN1C(=O)CCC1.Cl>O1CCOCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([OH:13])[CH:7]=[C:6]2[NH:19][C:18]1[CH:20]=[CH:21][C:22]([Cl:23])=[C:16]([Cl:15])[CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 72573,4-DichloroanilineHCID 13387N-methyl-2-pyrrolidoneHCID 178488025HCID 178488025, compound

Product 1

HCID 178488024HCID 178488024, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

6-Methoxyquinolinediol (2.5 g, 13.08 mmol) and 3,4-dichloroaniline (4.2 g, 26.25 mmol) were placed in a 100 mL Teflon vessel for use with an Ethos 1600 Lab Microwave. NMP was then added (9 mL), followed by HCl in dioxane (5 mL, 4 M). The slurry was irradiated to achieve a 200° C. temperature using a 400 W upper setpoint for 30 min. The mixture was cooled, suspended in methanol (20 mL), and filtered to afford 1.049 g of the title compound. 1H NMR (300 MHz, DMSO): 3.84 (s, 3H), 5.84 (s, 1H), 7.23 (td, ?H, J=8.88, 8.48 Hz), 7.35(tt, ?H, J=8.88, 2.42 Hz), 7.56(d, ?H, J=2.42 Hz), 7.66 (˜s, 2H), 8.71(s, 1H), 11.10(s, 1H).

Workup

  1. customThe slurry was irradiated
  2. customto achieve a 200° C.
  3. customfor 30 min
  4. temperatureThe mixture was cooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-a57a86d4070e4ebba8bc59a9216e7486
Source dataset
uspto-grants-2006_12
Patent number
US07153865B2

Reaction notes

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