Hydrochloric Acid → HCID 23630708, compound

HRID 917758Notes

Reaction equation

HRID 917758 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH2:11].Cl[C:13]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][N:16]=[C:15]([Cl:24])[CH:14]=1.Cl>CCO>[Cl:24][C:15]1[CH:14]=[C:13]([NH:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 70572-NaphthylamineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

Product 1

HCID 23630708HCID 23630708, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Naphthylamine and ethyl 4,6-dichloronicotinate were reacted in a mixture of EtOH and conc. HCl as for example 33, step A. The resultant solid was isolated by filtration and washed with 10% Et2O/Hexane, yielding ethyl 6-chloro-4-(2-naphthylamino)nicotinate (68%). 1H NMR [400 MHz, (CD3)2SO] δ 9.91 (br s, 1H), 8.71 (s, 1H), 8.02 (d, J=8.7 Hz, 1H), 7.97-7.88 (m, 3H), 7.59-7.48 (m, 3H), 6.91 (s, 1H), 4.39 (q, J=7.1 Hz, 2H), 1.37 (t, J=7.1 Hz, 3H).

Workup

  1. customThe resultant solid was isolated by filtration
  2. washwashed with 10% Et2O/Hexane

Sources & evidence

ORD record
ord-28085c662efa44999b6b1436cb0a7903
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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