Hydrazine hydrate (1:1) → 6-[(3-Methyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-3-pyridinamine

HRID 527577Notes

Reaction equation

HRID 527577 reaction equation
O.NN.[CH3:4][CH:5]1[C:9]2[C:10]([O:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][N:16]=3)=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][O:6]1>C(O)C.[Pd]>[CH3:4][CH:5]1[C:9]2[C:10]([O:14][C:15]3[N:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=3)=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][O:6]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 679606462-[(3-Methyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-5-nitropyridine2×

Product 1

HCID 679606486-[(3-Methyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-3-pyridinamineYield 93.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

In a 50 ml round-bottomed flask 2-[(3-methyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-5-nitropyridine (Intermediate 99, 38.3 mg) was dissolved in ethanol (10 ml) to give a pale yellow solution. Pd/C (14.22 mg, 0.013 mmol) and hydrazine hydrate (0.026 ml, 0.267 mmol) were added. The reaction mixture was stirred at 90° C. After 45 minutes, the reaction mixture was filtered and the organic phase was evaporated under vacuum to afford the title compound (32 mg).

Workup

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

Sources & evidence

ORD record
ord-9b6725387e184a65b82a608506962a9c
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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