Acetic Acid → HCID 23631005, compound

HRID 917759Notes

Reaction equation

HRID 917759 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)[CH:15]=2)[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.[CH3:42][CH2:43][OH:44]>C(Cl)(Cl)Cl>[CH3:2][N:3]1[C:43](=[O:44])[CH:42]=[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)[CH:15]=2)[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 702EthanolHCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 23630708HCID 23630708, compound

Product 1

HCID 23631005HCID 23631005, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl 6-chloro-4-(2-naphthylamino)nicotinate was dissolved in CHCl3 and reacted with Me2SO4, followed by triethylamine, AcOH and EtOH as described for example 33, step B. Purification by recrystallisation (EtOAc/Hexane) afforded ethyl 1-methyl-4-(2-naphthylamino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate as a white solid (57%); m.p. (EtOAc/Hexane) 160-163° C. 1H NMR [400 MHz, (CD3)2SO] δ 9.55 (s, 1H), 8.57 (s, 1H), 7.97 (d, J=8.8 Hz, 1H), 7.91 (dd, J=7.7, 4.7 Hz, 2H), 7.81 (d, J=1.8 Hz, 1H), 7.55-7.43 (m, 3H), 5.79 (s, 1H), 4.32 (q, J=7.1 Hz, 2H), 3.43 (s, 3H), 1.35 (t, J=7.1 Hz, 3H). Anal. Calcd for C19H18N2O3: C, 70.8; H, 5.6; N, 8.7. Found C, 70.8; H, 5.5; N, 8.7.

Workup

  1. customPurification
  2. customby recrystallisation (EtOAc/Hexane)

Sources & evidence

ORD record
ord-f3017a3440d04b13906e7abf66d82865
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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