Hydrazine hydrate (1:1) → 6-[(3-methyl-3,4-dihydro-2H-chromen-5-yl)oxy]-3-pyridinamine

HRID 527590Notes

Reaction equation

O.NN.[CH3:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][N:17]=2)[O:7][CH2:6]1>C(O)C.[Pd]>[CH3:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:15][C:16]2[N:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=2)[O:7][CH2:6]1

Participants

Conditions

Temperature: 90 °C

Procedure

In a 50 ml round-bottomed flask 2-[(3-methyl-3,4-dihydro-2H-chromen-5-yl)oxy]-5-nitropyridine (Intermediate 118, 181 mg) was dissolved in ethanol (10 ml) to give a pale yellow solution. Pd/C (33.0 mg, 0.031 mmol) and hydrazine hydrate (0.030 ml, 0.310 mmol) were added. The reaction mixture was stirred at 90° C. After 1 hour, the reaction mixture was filtered and evaporated under vacuum to give the title compound (131.4 mg).

Workup

customto give a pale yellow solution
filtrationthe reaction mixture was filtered
customevaporated under vacuum

Sources & evidence

ORD record: ord-4876bf9f11934fcb81c82154038dee93
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346790B2

Reaction notes

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