1-(4-Tert-butylphenyl)-2-chloroethan-1-one → HCID 57832783, compound

HRID 729496Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

2-Amino-3-bromopyridine (0.250 g, 1.45 mmol) and 4-tert-butylphenacyl chloride (0.306 g, 1.45 mmol) were dissolved in isopropanol (4.5 mL) and treated with sodium bicarbonate (0.146 g, 1.74 mmol). The mixture was stirred in a sealed tube at 80° C. for 48 h. The mixture was concentrated under reduced pressure and redissolved in ethyl acetate (30 mL). The organic mixture was washed with water and saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by flash silica gel chromatography, eluting with 10% acetone/hexane to give 0.370 g (77%) of the title compound. HPLC (Method B): r.t.=10.7 min., purity 100% at 210-370 nm, 99.3% at 252 nm. HRMS: calcd for C17H17BrN2+H+, 329.06478; found (ESI, [M+H]+), 329.0662.

Workup

concentrationThe mixture was concentrated under reduced pressure
dissolutionredissolved in ethyl acetate (30 mL)
washThe organic mixture was washed with water and saturated sodium chloride
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude material was purified by flash silica gel chromatography
washeluting with 10% acetone/hexane

Sources & evidence

ORD record: ord-c7b94db514f54971ad0bd52511eb35dd
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582636B2

Reaction notes

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