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

HRID 527582Notes

Reaction equation

O.NN.[CH2:4]([CH:6]1[C:10]2[C:11]([O:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][N:17]=3)=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][O:7]1)[CH3:5]>C(O)C.[Pd]>[CH2:4]([CH:6]1[C:10]2[C:11]([O:15][C:16]3[N:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=3)=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][O:7]1)[CH3:5]

Participants

Conditions

Temperature: 90 °C

Procedure

In a 50 ml round-bottomed flask 2-[(3-ethyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-5-nitropyridine (Intermediate 107, 97.6 mg) was dissolved in ethanol (10 ml) to give a pale yellow solution. Pd/C (26.1 mg, 0.245 mmol) and hydrazine hydrate (12.29 mg, 0.245 mmol) were added. The reaction mixture was stirred at 90° C. After 45 minutes, the reaction was completed. The reaction mixture was filtered and the organic phase was evaporated under vacuum affording the crude product which was charged on a 2 g SCX cartridge. It was then flushed with 15 ml of methanol followed by 15 ml of a 2M solution of ammonia in methanol. The ammonia eluate was evaporated under vacuum affording nothing. The methanol eluate was then evaporated under vacuum to afford the title compound as a colourless oil.

Workup

customto give a pale yellow solution
filtrationThe reaction mixture was filtered
customthe organic phase was evaporated under vacuum
customaffording the crude product which
additionwas charged on a 2 g SCX cartridge
customIt was then flushed with 15 ml of methanol
customThe ammonia eluate was evaporated under vacuum
customaffording nothing
customThe methanol eluate was then evaporated under vacuum

Sources & evidence

ORD record: ord-bc3d828d3a0b4acfabda976596435dfc
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346790B2

Reaction notes

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