Acetic Acid → HCID 68920264, compound

HRID 1879817Notes

Reaction equation

HRID 1879817 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:3]=1.[NH2:22][NH2:23].[C:24]1([CH3:32])[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=O)[CH:25]=1.C(O)(=O)C>O1CCOCC1.C(Cl)Cl>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[C:4]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[CH:3]=[C:2]2[NH:22][N:23]=[CH:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([CH3:32])[CH:25]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 9321HydrazineHCID 121053-MethylbenzaldehydeHCID 57935895HCID 57935895, compound

Product 1

HCID 68920264HCID 68920264, compoundYield 36.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of compound C (33 mg, 0.1 mmol) in 3 mL of dioxane was added an excess amount of hydrazine (0.02 mL, 0.65 mmol). The resulting mixture was heated at 90° C. for 2 h. The reaction mixture was cooled to room temperature and diluted with methylene chloride, followed by washing with brine twice. The organic phase was dried and concentrated. The left residue was dried in vacuo, and then dissolved in 5 mL of methanol. To the above solution was added m-tolualdehyde (0.01 mL, 0.11 mmol) and a catalytic amount of acetic acid. After the reaction mixture was heated at 50° C. for 30 min, the mixture was cooled to room temperature. A small amount of precipitate was observed and collected to give 15 mg of the final product, N-(6,7-Dimethoxy-2-morpholin-4-yl-quinolin-4-yl)-N′-(3-methyl-benzylidene)-hydrazine (compound 7).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washby washing with brine twice
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customThe left residue was dried in vacuo
  6. dissolutiondissolved in 5 mL of methanol
  7. temperatureAfter the reaction mixture was heated at 50° C. for 30 min
  8. temperaturethe mixture was cooled to room temperature
  9. customcollected

Sources & evidence

ORD record
ord-449753041f6e4e7c93456c0c5be31b1a
Source dataset
uspto-grants-2012_11
Patent number
US08318730B2

Reaction notes

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