Pyridine → 2-Valerylamino-5-bromo-4-methyl-3-nitropyridine

HRID 975306Notes

Reaction equation

[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[C:5]([Br:12])=[CH:4][N:3]=1.N1C=CC=CC=1.[C:19](Cl)(=[O:24])[CH2:20][CH2:21][CH2:22][CH3:23].C(Cl)Cl>O>[C:19]([NH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[C:5]([Br:12])=[CH:4][N:3]=1)(=[O:24])[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture comprising 10 g (43.1 mmol) of 2-amino-5-bromo-4-methyl-3-nitropyridine and 6.8 g of pyridine was heated to 110° C. in a nitrogen atmosphere. 5.7 g (47.4 mmol) of valeroyl chloride was dropwise added thereto and The mixture was stirred at 110° C. for 5 hours. The reaction mixture was brought to room temperature, followed by the addition of methylene chloride (50 ml) and water (50 ml). The organic phase was separated. The aqueous phase was further extracted with methylene chloride (50 ml). The organic phases were combined, dried over anhydrous magnesium sulfate and subjected to vacuum concentration to give a crude crystal. It was recrystallized from ethyl acetate to give 11 g of 2-valerylamino-5-bromo-4-methyl-3-nitropyridine (yield 81%).

Workup

customwas brought to room temperature
customThe organic phase was separated
extractionThe aqueous phase was further extracted with methylene chloride (50 ml)
dry with materialdried over anhydrous magnesium sulfate
concentrationsubjected to vacuum concentration
customto give a crude crystal
customIt was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-8f3a3a13413b4635ab0f9da4eb40add3
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05608068

Reaction notes

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