7-Aminoquinoline → HCID 22135529, compound

HRID 2113083Notes

Reaction equation

HRID 2113083 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.[NH2:19][C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][CH:26]=[N:27]2)=[CH:22][CH:21]=1>CCOC(C)=O.[Cl-].[Cl-].[Zn+2]>[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:19][C:20]2[CH:29]=[C:28]3[C:23]([CH:24]=[CH:25][CH:26]=[N:27]3)=[CH:22][CH:21]=2)=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 113777-AminoquinolineHCID 21865297HCID 21865297, compound2×

Product 1

HCID 22135529HCID 22135529, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
220 °C

Procedure

(Analogous to the procedure of WO 178270). A mixture of 3,6-dichloro-4-(4-trifluoromethylphenyl)pyridazine, Example 81(d), (2.0 g, 6.8 mmol), 7-amino-quinoline (984 mg, 6.8 mmol) and ZnCl2 (980 mg, 3.4 mmol) was heated in a microwave with stirring at 220° C. for 20 min. The reaction mixture was cooled to room temperature, a second portion of 3,6-dichloro-4-(4-trifluoromethylphenyl)pyridazine (2.0 g, 6.8 mmol), was added and the mixture was heated again in microwave at 220° C. for 40 min. The reaction mixture was cooled to room temperature, diluted with EtOAc (50 mL) and washed with H2O (3×). The organic layer was dried over Na2SO4, filtered and the solvent evaporated in vacuo. The residue was purified by preparative thin layer chromatography, eluting with MeOH:CH2Cl2 (1:39), to give the title compound as a light-yellow powder. MS (ESI, pos. ion) m/z: 401 (M+1).

Workup

  1. temperaturewas heated in a microwave
  2. temperatureThe reaction mixture was cooled to room temperature
  3. temperaturethe mixture was heated again in microwave at 220° C. for 40 min
  4. temperatureThe reaction mixture was cooled to room temperature
  5. washwashed with H2O (3×)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo
  9. customThe residue was purified by preparative thin layer chromatography
  10. washeluting with MeOH:CH2Cl2 (1:39)

Sources & evidence

ORD record
ord-e94b40d5d8184a67a9a5487cb39b08fb
Source dataset
uspto-grants-2009_04
Patent number
US07524874B2

Reaction notes

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