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

HRID 1526140Notes

Reaction equation

HRID 1526140 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 intermediate 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 subjected to microwave heating at 150° C. for 1 min. After cooling, additional hydrazine monohydrate (1 eq) was added to the resulting mixture, which was then subjected to microwave heating at 150° C. 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. temperatureto microwave heating at 150° C. 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-c09e35355658427e8fb405ea19a15912
Source dataset
uspto-grants-2015_07
Patent number
US09085577B2

Reaction notes

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