Acetic Acid → Ethyl 4-[(1-chloro-2-naphthyl)amino]-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate

HRID 917763Notes

Reaction equation

HRID 917763 reaction equation
Cl[C:2]1C=[C:11]([NH:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[Cl:24])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.COS(OC)(=O)=O.C(N(CC)CC)C.CC(O)=O.[CH3:43][CH2:44][OH:45]>C(Cl)(Cl)Cl>[Cl:24][C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[NH:13][C:11]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]([CH3:2])[C:44](=[O:45])[CH:43]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 702EthanolHCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 86596381Ethyl 6-chloro-4-[(1-chloro-2-naphthyl)amino]nicotinate

Product 1

HCID 69508838Ethyl 4-[(1-chloro-2-naphthyl)amino]-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylateYield 71%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl 6-chloro-4-[(1-chloro-2-naphthyl)amino]nicotinate was dissolved in CHCl3 and reacted with Me2SO4, followed by triethylamine, AcOH and EtOH as described for example 33, step B. Purification by flash chromatography on silica gel (50% EtOAc/Hexane) afforded ethyl 4-[(1-chloro-2-naphthyl)amino]-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate (71%). 1H NMR [400 MHz, (CD3)2SO] δ 9.73 (s, 1H), 8.59 (s, 1H), 8.18 (d, J=8.4 Hz, 1H), 8.02 (t, J=8.4 Hz, 2H), 7.75-7.69 (m, 2H), 7.64-7.59 (m, 1H), 5.59 (s, 1H), 4.34 (q, J=7.1 Hz, 2H), 3.45 (s, 3H), 1.35 (t, J=7.1 Hz, 3H).

Workup

  1. customPurification by flash chromatography on silica gel (50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-766b2d1ba38f49e19170ad36de1bf2e5
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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