Aniline → Ethyl 6-chloro-4-(phenylamino)nicotinate

HRID 424706Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:13])[C:5]1[C:10](Cl)=[CH:9][C:8]([Cl:12])=[N:7][CH:6]=1)[CH3:2].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[C:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][C:8]([Cl:12])=[N:7][CH:6]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

4,6-Dichloronicotinic acid ethyl ester 16 (500 mg, 2.27 mmol) is dissolved in anhydrous dioxane (10 mL) and aniline (0.66 mL, 7.72 mmol) is added. The reaction is stirred at 100° C. overnight. The solvent is removed in vacuo and the crude product is purified using flash chromatography (hexane:ethyl acetate=10:1) to give 6-chloro-4-phenylamino-nicotinic acid ethyl ester 17. 1H NMR (400 MHz, CDCl3) δ 9.77 (s, 1H), 8.70 (s, 1H), 7.33-7.37 (m, 2H), 7.15-7.21 (m, 3H), 6.80 (s, 1H), 4.31 (q, 2H), 1.34 (t, 3H).

Workup

customThe solvent is removed in vacuo
customthe crude product is purified

Sources & evidence

ORD record: ord-b179701f9c6846339c037d118f30dc9f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106068B2

Reaction notes

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