Diethyl Ether → 6-[Ethyl-(5,5,8-trimethyl-5,6-dihydro-naphthalen-2-yl)-amino]-nicotinic acid

HRID 1166692Notes

Reaction equation

[CH2:1]([NH:3][C:4]1[CH:13]=[CH:12][C:11]2[C:10]([CH3:15])([CH3:14])[CH2:9][CH:8]=[C:7]([CH3:16])[C:6]=2[CH:5]=1)[CH3:2].F[C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][N:19]=1.CCOCC>C1(C)C=CC=CC=1>[CH2:1]([N:3]([C:4]1[CH:13]=[CH:12][C:11]2[C:10]([CH3:15])([CH3:14])[CH2:9][CH:8]=[C:7]([CH3:16])[C:6]=2[CH:5]=1)[C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][N:19]=1)[CH3:2]

Participants

Conditions

Temperature: 125 °C

Procedure

To a mixture of 1.78 g (8.3 mmol) of ethyl-(5,5,8-trimethyl-5,6-dihydro-naphthalen-2-yl)-amine (Compound 166) and 0.55 g (3.9 mmol) of 6-fluoro-nicotinic acid was added a small amount of ether and toluene to help stirring. The resulting mixture was heated at 100-150° C. for 1 h. The mixture was cooled. The product was purified by flash chromatography (silica, 50% ethyl acetate in hexanes) followed by recrystallization using ethyl acetate:hexane (1:1) to give the title compound as white crystals (158 mg).

Workup

temperatureThe mixture was cooled
customThe product was purified by flash chromatography (silica, 50% ethyl acetate in hexanes)
customfollowed by recrystallization

Sources & evidence

ORD record: ord-1b1026bdaf164045883179f349562783
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613917B1

Reaction notes

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