Pyridine → 3-iodo-6,7,8,9-tetrahydrobenzocylohepten-5-one-O-methyl-oxime

HRID 241509Notes

Reaction equation

[I:1][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=O)[C:4]=2[CH:3]=1.N1C=CC=CC=1.Cl.[CH3:21][O:22][NH2:23]>CO>[CH3:21][O:22][N:23]=[C:10]1[C:4]2[CH:3]=[C:2]([I:1])[CH:13]=[CH:12][C:5]=2[CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

Conditions

Temperature: 20 °C

Procedure

To a stirred suspension of 3-iodo-6,7,8,9-tetrahydrobenzocylohepten-5-one prepared as described in example P3a (0.806 g; 2.82 mmol) in methanol (5.7 ml) was added pyridine (0.7 ml; 9.02 mmol) followed by a portion wise addition of methoxyamine hydrochloride (0.754 g; 9.02 mmol). The reaction mixture was stirred at 20° C. for 16 h under nitrogen. The solvent was removed in vacuo to afford 0.86 g (97% of theory) of crude 3-iodo-6,7,8,9-tetrahydrobenzocylohepten-5-one-O-methyl-oxime E/Z-mixture as a brown oil.

Workup

customprepared
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-88488df4619e45038cbaf9d37fa9c83f
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653003B2

Reaction notes

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