Hydrazine hydrate (1:1) → HCID 178435583, compound

HRID 1921358Notes

Reaction equation

C[N:2]([CH:4]=[N:5][C:6](=O)[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[C:10]([O:15][CH3:16])=[N:9][C:8]=1[CH3:17])C.O.[NH2:20]N>C(O)(=O)C>[CH2:13]([C:11]1[C:10]([O:15][CH3:16])=[N:9][C:8]([CH3:17])=[C:7]([C:6]2[N:5]=[CH:4][NH:2][N:20]=2)[CH:12]=1)[CH3:14]

Participants

Conditions

Temperature: 90 °C

Procedure

In a round bottom flask under a nitrogen atmosphere N-dimethylaminomethylene-5-ethyl-6-methoxy-2-methylnicotinamide (synthesized on 0.309 mmol scale) is treated with glacial acetic acid (1 mL) followed by hydrazine hydrate (16.5 μL, 0.340 mmol). The resulting mixture is stirred at 90° C. for 3.75 hr. The reaction mixture is evaporated, then partitioned between water and dichloromethane and the pH adjusted to 6-7 by treating with solid sodium bicarbonate. The aqueous layer is separated and then further extracted with five portions of dichloromethane. The combined extract is dried over magnesium sulfate, filtered and evaporated to give 3-ethyl-2-methoxy-6-methyl-5-(1H-1,2,4-triazol-3-yl)-pyridine (35 mg, 52% yield, 2 steps) as a white solid. MS: m/e=219 (M+H); 1H NMR (300 MHz, CDCl3, δ, ppm): 11.52 (1H, s), 8.18 (1H, s), 7.78 (1H, s), 3.98 (3H, s), 2.68 (3H, s), 2.57 (2H, q), 1.19 (3H, t).

Workup

customThe reaction mixture is evaporated
custompartitioned between water and dichloromethane
additionby treating with solid sodium bicarbonate
customThe aqueous layer is separated
extractionfurther extracted with five portions of dichloromethane
extractionThe combined extract
dry with materialis dried over magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-f8e250c56ef941f2a1021429800e7c13
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173682B2

Reaction notes

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