Hydrazine hydrate (1:1) → HCID 16788418, compound

HRID 1505320Notes

Reaction equation

HRID 1505320 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:3].O.NN>C(O)C.[Pd]>[CH3:3][CH:2]([C:4]1[CH:5]=[C:6]([O:10][C:11]2[N:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:1]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 28254339HCID 28254339, compound2×

Product 1

HCID 16788418HCID 16788418, compoundYield 66.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-{[3-(1-methylethyl)phenyl]oxy}-5-nitropyridine (Intermediate 23, 1.39 g) was dissolved in ethanol (25 mL). Hydrazine monohydrate (0.524 mL, 1076 mmol) and palladium on carbon (401 mg, 0.377 mmol) were added. The reaction mixture was heated at reflux under argon for 1 hour. The reaction was cooled down and then filtered on celite. The organic phase was evaporated under vacuum. The residue was purified by flash chromatography on silica (Companion instrument, 120 g silica cartridge, gradient cyclohexane/ethylacetate from 100/0 to 30/70 in 15 min then 30/70 during 30 min). Evaporation afforded the title compound as a yellow oil (821 mg).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under argon for 1 hour
  3. temperatureThe reaction was cooled down
  4. filtrationfiltered on celite
  5. customThe organic phase was evaporated under vacuum
  6. customThe residue was purified by flash chromatography on silica (Companion instrument, 120 g silica cartridge, gradient cyclohexane/ethylacetate from 100/0 to 30/70 in 15 min
  7. customEvaporation

Sources & evidence

ORD record
ord-f9478a22c6ab454999155dd66e3f01c3
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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