1,3-Cyclohexanedione → 3-(3-Carbomethoxy-2-bromoanilino)cyclohex-2-en-1-one

HRID 1775196Notes

Reaction equation

[NH2:1][C:2]1[C:3]([Br:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:13]1(=O)[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH2:14]1>C(O)(=O)C>[Br:12][C:3]1[C:2]([NH:1][C:13]2[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH:14]=2)=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 3-amino-2-bromobenzoate (2.39 g, 10.0 mmol) and cyclohexane-1,3-dione (1.12 g, 10.0 mmol) were dissolved in 10 mL of acetic acid at 25° C., under nitrogen. The mixture was stirred at 80° C. for 8 hours. The resultant solid was purified by chromatography column on silica gel (elution with hexane/ethyl acetate) to afford 2.46 g (76%) of methyl 2-bromo-3-((3-oxocyclohex-1-en-1-yl)amino)benzoate as a tan foam. 1H NMR (CDCl3-d1) δ 7.53-7.55 (m, 2H), 7.37 (dd, 1H, J=7.2, 8.4 Hz), 6.34 (br s, 1H), 5.57 (s, 1H), 3.95 (s, 3H), 2.56-2.59 (m, 2H), 2.40-2.42 (m, 2H), and 2.08-2.11 (m, 2H). MS (ESI) m/e [M+1]+ 324.0.

Workup

customThe resultant solid was purified by chromatography column on silica gel (elution with hexane/ethyl acetate)

Sources & evidence

ORD record: ord-51f9567304794665b349f2b9a435824f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260440B2

Reaction notes

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