Potassium Hydroxide → 3-Amino-4-ethylamino-6-(3-trifluoromethylphenyl)-pyridine-2-carbonitrile

HRID 2246456Notes

Reaction equation

O.O.[Sn](Cl)(Cl)(Cl)Cl.[CH2:8]([NH:10][C:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[N:14]=[C:13]([C:27]#[N:28])[C:12]=1[N+:29]([O-])=O)[CH3:9].[OH-].[K+]>Cl.CN(C=O)C>[NH2:29][C:12]1[C:13]([C:27]#[N:28])=[N:14][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=2)=[CH:16][C:11]=1[NH:10][CH2:8][CH3:9]

Participants

Conditions

Temperature: 5 °C

Procedure

At 0° C., a solution of tin chloride dihydrate (30.2 g) in concentrate aqueous HCl (150 mL) was added dropwise over 2 hours to a solution of 4-ethylamino-3-nitro-6-(3-trifluoromethyl-phenyl)-pyridine-2-carbonitrile (5.0 g) in DMF (100 mL). The mixture was further stirred for 1 hour at 5° C., then poured to a mixture of ice (900 g) and potassium hydroxide (440 g), extracted with ethyl acetate (2×1.4 L). The combined organic layers were washed with brine (700 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound (4,56 g) as a solid. 1H NMR (DMSO-d6) δ: 8.30-8.20 (m, 2H); 7.75-7.60 (m, 2H); 7.08 (s, 1H); 6.11 (t, J=6 Hz, 1H); 5.95 (br. s, 2H); 3.4-3.3 (m, 2H); 1.27 (t, J=7 Hz, 3H).

Workup

extractionextracted with ethyl acetate (2×1.4 L)
washThe combined organic layers were washed with brine (700 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-641d5236e6f341cdb07ac62fa548f377
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687515B2

Reaction notes

Loading…