Hydrazine → 4-Hydrazino-2-(trifluoromethyl)quinazoline

HRID 2063590

Reaction equation

HRID 2063590 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[N:3]=1.[NH2:16][NH2:17].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[F:13][C:12]([F:15])([F:14])[C:4]1[N:3]=[C:2]([NH:16][NH2:17])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 11430Potassium CarbonateHCID 14754354-chloro-2-(trifluoromethyl)quinazoline

Product 1

HCID 14754644-Hydrazino-2-(trifluoromethyl)quinazolineYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-2-(trifluoromethyl)quinazoline (2.0 g, 8.6 mmol) and hydrazine (0.27 mL, 8.6 mmol) in 20 mL of tetrahydrofuran was added 1.8 g (13 mmol) of potassium carbonate. The resultant suspension was stirred at ambient temperature for 2 hours. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and the combined organics were dried over magnesium sulfate. After filtration, the organics were concentrated in vacuo to yield a yellow solid that was recrystallized in ethyl acetate:hexanes. 1.1 g (56%) of yellow needle-like crystals were isolated.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organics were dried over magnesium sulfate
  4. filtrationAfter filtration
  5. concentrationthe organics were concentrated in vacuo
  6. customto yield a yellow solid
  7. customthat was recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-393a81e8894d48a09d519c362141752b
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Linked notes

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