HCID 59612107, compound → 6-(4-Chlorophenyl)-4-oxo-1,4,5,6-tetrahydropyridine-2-carboxylic acid ethyl ester

HRID 889653Notes

Reaction equation

HRID 889653 reaction equation
[CH2:1]([O:3][C:4](=[O:19])/[C:5](/[NH2:18])=[CH:6]/[C:7](=[O:17])/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[CH3:2]>O1CCOCC1>[CH2:1]([O:3][C:4]([C:5]1[NH:18][CH:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:8][C:7](=[O:17])[CH:6]=1)=[O:19])[CH3:2]

Participants

3

Reactant 1

HCID 59612107HCID 59612107, compound

Product 1

HCID 596121216-(4-Chlorophenyl)-4-oxo-1,4,5,6-tetrahydropyridine-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Using the procedure of Example 5, (2Z,5E)-2-amino-6-(4-chlorophenyl)-4-oxo-hexa-2,5-dienoic acid ethyl ester (8; 47 g, 0.168 mol) in 1,4-dioxane (470 mL) in a 2 liter Parr reactor gave, following purification by silica gel chromatography eluting with 40% EtOAc/hexanes, 6-(4-chlorophenyl)-4-oxo-1,4,5,6-tetrahydropyridine-2-carboxylic acid ethyl ester (12; 25 g, 49%, 99% pure by HPLC) as an off-white solid: mp 93-94° C.; 1H NMR (400 MHz, CDCl3) δ 7.36 (q, J=8.6 Hz, 4H), 5.82 (s, 1H), 5.72 (br s, 1H), 4.74 (dd, J=14.2, 5.0 Hz, 1H), 4.35 (q, J=7.1 Hz, 2H), 2.68 (dd, J=16.3, 14.2 Hz, 1H), 2.58 (dd, J=16.4, 5.0 Hz, 1H), 1.36 (t, J=7.1 Hz, 3H); HRMS-ESI (m/z): calcd for C14H14ClNO3, 279.067. found, 279.066.

Workup

  1. customgave
  2. custompurification by silica gel chromatography
  3. washeluting with 40% EtOAc/hexanes, 6-(4-chlorophenyl)-4-oxo-1,4,5,6-tetrahydropyridine-2-carboxylic acid ethyl ester (12; 25 g, 49%, 99% pure by HPLC) as an off-white solid

Sources & evidence

ORD record
ord-a1417d120bc3444b8c9b5ede3faec237
Source dataset
uspto-grants-2012_08
Patent number
US08252938B2

Reaction notes

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