Hydrazine hydrate (1:1) → HCID 57459592, compound

HRID 587624Notes

Reaction equation

HRID 587624 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]#[N:16])=[C:13](Br)[N:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:19][NH2:20]>C1COCC1>[CH2:1]([O:8][C:9]1[C:14]([C:15]#[N:16])=[C:13]([NH:19][NH2:20])[N:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 230886954-(Benzyloxy)-2-bromonicotinonitrile

Product 1

HCID 57459592HCID 57459592, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of compound D2 (1.2 g, 4.15 mmol) in THF (12 ml) was added hydrazine monohydrate (0.416 g, 8.301 mmol). The reaction mixture was heated at 150° C. under microwave irradiation for 1 min. After cooling, additional hydrazine monohydrate (1 eq) was added to the reaction mixture, which was then heated at 150° C. under microwave irradiation for 0.5 min. After cooling, the reaction mixture was concentrated in vacuo. The residue thus obtained was triturated with Et2O to yield intermediate compound D3 (0.95 g, 95%).

Workup

  1. temperatureAfter cooling
  2. temperaturewas then heated at 150° C. under microwave irradiation for 0.5 min
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. customThe residue thus obtained
  6. customwas triturated with Et2O

Sources & evidence

ORD record
ord-1ff91ed268eb46aab8544ceb60362560
Source dataset
uspto-grants-2016_01
Patent number
US09226930B2

Reaction notes

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