Hydrazine hydrate (1:1) → HCID 16641867, compound

HRID 1505334Notes

Reaction equation

HRID 1505334 reaction equation
O.NN.[CH3:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][N:14]=1>C(O)C.[Pd]>[CH3:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[O:12][C:13]1[N:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 126759562-(2,6-Dimethylphenoxy)-5-nitropyridine2×

Product 1

HCID 16641867HCID 16641867, compoundYield 190.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

In a 50 mL round-bottomed flask 2-[(2,6-dimethylphenyl)oxy]-5-nitropyridine (Intermediate 41, 555.9 mg) was dissolved in ethanol (10 mL) to give a pale orange solution. Palladium on carbon (230 mg, 0.216 mmol) and hydrazine hydrate (0.416 mL, 4.32 mmol) were added. The reaction mixture was stirred at 90° C. After 3 hours the reaction was completed. The reaction mixture was filtered and the organic phase was evaporated under vacuum to afford 929.9 mg of a dark orange solid that was charged on a 10 g SCX cartridge. It was then flushed with 200 mL of ethanol followed by 50 mL of 2M solution of ammonia in MeOH. The ammonia eluate was evaporated under vacuum to afford the title compound as dark orange solid (447.6 mg).

Workup

  1. customto give a pale orange solution
  2. filtrationThe reaction mixture was filtered
  3. customthe organic phase was evaporated under vacuum

Sources & evidence

ORD record
ord-fca02dd9a8a14bf6abea1962f7c92256
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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