N-[4-(2-tert-butoxy-pyridin-4-yl)-benzyl]-2,6-dichloro-benzamide → 2,6-dichloro-N-[4-(2-oxo-1,2-dihydro-pyridin-4-yl)-benzyl]-benzamide

HRID 1042928Notes

Reaction equation

C([O:5][C:6]1[CH:11]=[C:10]([C:12]2[CH:29]=[CH:28][C:15]([CH2:16][NH:17][C:18](=[O:27])[C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])=[CH:14][CH:13]=2)[CH:9]=[CH:8][N:7]=1)(C)(C)C>C(O)=O>[Cl:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([Cl:25])[C:19]=1[C:18]([NH:17][CH2:16][C:15]1[CH:28]=[CH:29][C:12]([C:10]2[CH:9]=[CH:8][NH:7][C:6](=[O:5])[CH:11]=2)=[CH:13][CH:14]=1)=[O:27]

Participants

Conditions

Temperature: 40 °C

Procedure

N-[4-(2-tert-Butoxy-pyridin-4-yl)-benzyl]-2,6-dichloro-benzamide was dissolved in 30 mL dichloromethone and 12 mL of 98% formic acid. The mixture was stirred at 40° C. for three hours after which the volatile components were evaporated under vacuum. The residue was triturated with ethyl acetate, filtered, washed with ethyl acetate and dried giving 2,6-dichloro-N-[4-(2-oxo-1,2-dihydro-pyridin-4-yl)-benzyl]-benzamide (4.34 g, 75.5% yield over two steps) as white powder. C19H14Cl2N2O2; MS m/z: 373 (MH+) 1H NMR (DMSO-d6): δ 11.56 (s, 1H), δ 9.21 (t, J=5.6 Hz, 1H), δ 7.67 (d, J=8.0 Hz, 2H), δ 7.46 (m, 6H), δ 6.57 (d, J=1.2 Hz, 1H), δ 6.49 (dd, J=6.8 Hz, J′=1.6 Hz, 1H), δ 4.50 (d, J=6.0 Hz, 2H.

Workup

customwere evaporated under vacuum
customThe residue was triturated with ethyl acetate
filtrationfiltered
washwashed with ethyl acetate
customdried

Sources & evidence

ORD record: ord-68b78720eabd4038b74c0403811b06c0
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08558001B2

Reaction notes

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