Hydrazine hydrate (1:1) → HCID 28818304, compound

HRID 1505337Notes

Reaction equation

HRID 1505337 reaction equation
O.NN.[CH2:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][N:14]=1)[CH3:5]>C(O)C.[Pd]>[CH2:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[N:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=1)[CH3:5]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 40541027HCID 40541027, compound2×

Product 1

HCID 28818304HCID 28818304, compoundYield 208.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

In a 50 mL round-bottomed flask 2-[(2-ethylphenyl)oxy]-5-nitropyridine (Intermediate 45, 623 mg) was dissolved in ethanol (10 mL) to give a pale orange solution. Palladium on carbon (244 mg, 0.230 mmol) and hydrazine hydrate (0.442 mL, 4.59 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 affording 1.1408 g 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 (456.1 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-fbd3ea17c5ba4bc183336543daac9455
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

Loading…