Hydrazine hydrate (1:1) → HCID 67958758, compound

HRID 527670Notes

Reaction equation

HRID 527670 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][N:14]=2)[O:5][CH2:4][CH2:3]1.O.NN>C(O)C.[Pd]>[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[N:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=2)[O:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67958429HCID 67958429, compound2×

Product 1

HCID 67958758HCID 67958758, compoundYield 111.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

In a 50 mL round-bottomed flask 2-(4-methylchroman-5-yl)oxy-5-nitro-pyridine (Intermediate 212, 22.9 mg, 0.08 mmol) was dissolved in Ethanol (10 mL) to give a pale yellow solution. Pd/C (17.88 mg, 0.017 mmol) and hydrazine hydrate (0.4 mL, 4.15 mmol) were added. The reaction mixture was stirred at 90° C. The reaction mixture was filtered and evaporated in vacuo to give the title compound (22.9 mg) as a pale yellow oil.

Workup

  1. customto give a pale yellow solution
  2. filtrationThe reaction mixture was filtered
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-24ad9b34c71c4a718a76129553e52264
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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