Hydrochloric Acid → 5-Cyano-2-methyl-6-oxo-4-p-tolyl-1,2,3,6-tetrahydropyridine-2-carboxylic acid

HRID 1629805Notes

Reaction equation

[C:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:15])([C:10]([O:12]CC)=[O:11])[CH2:5][C:4]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)#[N:2].Cl>C(O)(=O)C>[C:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:15])([C:10]([OH:12])=[O:11])[CH2:5][C:4]=1[C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=1)#[N:2]

Participants

Conditions

Temperature: 60 °C

Procedure

Intermediate 108B (1.211 g, 4.06 mmol) was dissolved in acetic acid (95 mL) in a 250 mL 1 neck pear shaped flask that was equipped with a magnetic stirrer. HCl (11.67 mL, 142 mmol) was added and the reaction mixture was stirred at 60° C. overnight. The reaction mixture was concentrated in vacuo to give the desired product as a pale yellow solid. LCMS Anal. Calc'd for C15H14N2O3 270.1, found [M+H] 271.0. 1H NMR (500 MHz, CDCl3) δ 7.48 (d, J=8.3 Hz, 2H), 7.23 (d, J=7.7 Hz, 2H), 3.39 (d, J=18.2 Hz, 1H), 2.83 (d, J=18.2 Hz, 1H), 2.35 (s, 3H), 1.54 (s, 3H).

Workup

customwas equipped with a magnetic stirrer
concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-50aab3c1765d41079df0e89cb403cc96
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791091B2

Reaction notes

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