Hydrazine → 2-Hydrazinylquinazolin-4-amine

HRID 44372

Reaction equation

HRID 44372 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][NH2:14]>C(O)C>[NH:13]([C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[NH2:14]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 2528792-Chloroquinazolin-4-amine

Product 1

HCID 552804872-Hydrazinylquinazolin-4-amineYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-chloroquinazolin-4-amine (Example 38) (100 mg, 0.56 mmol) and hydrazine (0.09 mL, 2.79 mmol) in ethanol (5 mL) was heated in a sealed tube at 80° C. overnight. After the reaction mixture was cooled down, the resulting precipitate was collected by filtration, rinsed with ethanol and dried in the air to give the title compound (84 mg, 86%). 1H NMR (400 MHz, DMSO-d6) δ4.2 (bs, 2H), 4.6 (bs, 2H), 7.0 (t, J=7.2 Hz, 1H), 7.27 (d, J=8.0 Hz, 1H), 7.43 (s, 1H), 7.61 (s, 1H), 7.87 (d, J=7.6 Hz, 1H).

Workup

  1. temperatureAfter the reaction mixture was cooled down
  2. filtrationthe resulting precipitate was collected by filtration
  3. washrinsed with ethanol
  4. customdried in the air

Sources & evidence

ORD record
ord-8825132270bb4ac48c621bba3d01d5cb
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Linked notes

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