Hydrochloric Acid → 6-(4-Chloro-3-trifluoromethyl-phenoxy)-5-methyl-pyridin-3-ylamine

HRID 1894645Notes

Reaction equation

C(O)C.Cl.[Cl:5][C:6]1[CH:22]=[CH:21][C:9]([O:10][C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N+:18]([O-])=O)=[CH:13][N:12]=2)=[CH:8][C:7]=1[C:23]([F:26])([F:25])[F:24]>[Fe].O>[Cl:5][C:6]1[CH:22]=[CH:21][C:9]([O:10][C:11]2[N:12]=[CH:13][C:14]([NH2:18])=[CH:15][C:16]=2[CH3:17])=[CH:8][C:7]=1[C:23]([F:26])([F:24])[F:25]

Participants

Conditions

Temperature: 50 °C

Procedure

A 250 ml two-necked round-bottomed flask equipped with a KPG-stirrer, a thermometer and a reflux condenser is charged with ethanol (100 ml), water (10 ml), iron (3.11 g) and hydrochloric acid 37% (0.3 ml). The reaction mixture is heated at 50° C. 2-(4-chloro-3-trifluoromethyl-phenoxy)-3-methyl-5-nitro-pyridine (5.81 g) is added portionwise. The mixture was heated at reflux for 2 hours. After cooling the mixture to 50° C. it is filtered through celite. The filtrate is poured into water (200 ml) and extracted with ethylacetate (2×50 ml). The combined organic layers are washed with brine (100 ml), dried over sodium sulfate, filtered and the solvent is removed in vacuo to obtain 4.20 g of the compound as yellow solid (MP: 92-94° C.).

Workup

customA 250 ml two-necked round-bottomed flask equipped with a KPG-stirrer
temperatureThe mixture was heated
temperatureat reflux for 2 hours
temperatureAfter cooling the mixture to 50° C. it
filtrationis filtered through celite
additionThe filtrate is poured into water (200 ml)
extractionextracted with ethylacetate (2×50 ml)
washThe combined organic layers are washed with brine (100 ml)
dry with materialdried over sodium sulfate
filtrationfiltered
customthe solvent is removed in vacuo

Sources & evidence

ORD record: ord-4797254256bc4516a8ac837dc1118029
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513286B2

Reaction notes

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