Hydrazine hydrate (1:1) → HCID 59140362, compound

HRID 2092354Notes

Reaction equation

HRID 2092354 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]2[C:19]3[C:14](=[C:15]4[CH:23]=[CH:22][CH:21]=[CH:20][C:16]4=[CH:17][CH:18]=3)[NH:13][C:12](=[O:24])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.O.NN>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]2[C:19]3[C:14](=[C:15]4[CH:23]=[CH:22][CH:21]=[CH:20][C:16]4=[CH:17][CH:18]=3)[NH:13][C:12](=[O:24])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2854638HCID 2854638, compound

Product 1

HCID 59140362HCID 59140362, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred suspension of 4-(3-Nitro-phenyl)-3,4-dihydro-1H-benzo[h]quinolin-2-one (1.0 g, 3.14 mmol) and 10% Pd/C (0.10 g) in ethanol (50 ml) was slowly added hydrazine hydrate (0.40 g, 12.6 mmol). The solution was refluxed for 2 hr and the catalyst separated by filtration. The filtrate was concentrated in vacuo to 20 ml and the solution stored in a refrigerator overnight. The precipitate was separated by filtration, washed with small amount of ethanol and vacuum dried to afford the product (0.77 g, 2.67 mmol).

Workup

  1. temperatureThe solution was refluxed for 2 hr
  2. customthe catalyst separated by filtration
  3. concentrationThe filtrate was concentrated in vacuo to 20 ml
  4. customstored in a refrigerator overnight
  5. customThe precipitate was separated by filtration
  6. washwashed with small amount of ethanol and vacuum
  7. customdried

Sources & evidence

ORD record
ord-90599d0c03e24aa99982a56684d3a11f
Source dataset
uspto-grants-2013_05
Patent number
US08440705B2

Reaction notes

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