Hydrazine → HCID 11702079, compound

HRID 1668797Notes

Reaction equation

HRID 1668797 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:22][NH2:23]>O1CCOCC1>[NH:22]([C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[NH2:23]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 117381122-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine

Product 1

HCID 11702079HCID 11702079, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2-chloro-quinazolin-4-yl)-(4-methoxy-phenyl)-methylamine (100 mg, 0.33 mmol) in 2 ml of 1,4-dioxane was added 0.4 ml of hydrazine. The reaction mixture was stirred at room temperature overnight. After evaporating the solvent, the residue was diluted with EtOAc (20 ml), washed with saturated NaHCO3 aq., brine, dried over Na2SO4, filtered and concentrated by vacuum, yielding 20 mg (21%) of yellow solids. 1H NMR (CDCl3): 7.52-7.49 (m, 1H), 7.44-7.39 (m, 1H), 7.12-7.08 (m, 2H), 6.93-6.88 (m, 3H), 6.77-6.71 (m, 1H), 6.01 (brs, 1H), 4.11 (brs, 2H), 3.83 (s, 3H), 3.50 (s, 3H).

Workup

  1. customAfter evaporating the solvent
  2. additionthe residue was diluted with EtOAc (20 ml)
  3. washwashed with saturated NaHCO3 aq., brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated by vacuum

Sources & evidence

ORD record
ord-4787f676509d464cbe7573b783dc309b
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

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