Hydrazine hydrate (1:1) → HCID 178509390, compound

HRID 1518287Notes

Reaction equation

HRID 1518287 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](OC)=[C:16]([C:19]#[N:20])[C:17]#[N:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:24][NH2:25]>CCO>[NH2:18][C:17]1[NH:25][N:24]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[C:16]=1[C:19]#[N:20]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59447591HCID 59447591, compound

Product 1

HCID 178509390HCID 178509390, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 31C (3.1 g, 10.68 mmol) was dissolved in EtOH (20 mL). To this solution was added hydrazine hydrate (0.622 mL, 12.81 mmol). The reaction was heated under reflux for 2 hours. The solvent was removed, and the residue was taken up into EtOAc. It was then washed with water, brine, dried over MgSO4, and concentrated under reduced pressure to provide 2.72 g of the desired product: 1H NMR (DMSO-d6): δ 12.64 and 11.99 (s, 1H), 7.71-7.74 (m, 2H), 7.32-7.48 (m, 5H), 7.09-7.10 (br, 2H), 6.38 (s, 2H), 5.15 (s, 2H). MS (DCI(+)): m/z 291 (M+H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was removed
  4. washIt was then washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-09d5397cce744b7b953594607d31b632
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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