Acetic Acid → 4-(3-Dimethylamino-prop-1-ynyl)-3-trifluoromethyl-phenylamine

HRID 1660976Notes

Reaction equation

[CH3:1][N:2]([CH3:19])[CH2:3][C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[C:15]([F:18])([F:17])[F:16].CC(O)=O.O.N>[Fe].CCO>[CH3:19][N:2]([CH3:1])[CH2:3][C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[C:15]([F:16])([F:17])[F:18]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of dimethyl-[3-(4-nitro-2-trifluoromethyl-phenyl)-prop-2-ynyl]-amine (2.0 g, 7.4 mmol), iron powder (1.65 g, 29.4 mmol, 4 equiv), AcOH (5 mL), H2O (10 mL), and EtOH (40 mL) is stirred for 30 min at 80° C. The reaction mixture is allowed to cool to rt, basified by addition of a 1 M aqueous solution of NH3, and filtered through Celite. The filtrate is partially concentrated and extracted with EtOAc. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (CH2Cl2/NH3 (2 N in MeOH), 95:5) to provide the title compound as a brown oil: ES-MS: 243.0 [M+H]+; single peak at tR=2.49 min (System 1); Rf=0.10 (CH2Cl2/NH3 (2 N in MeOH), 95:5).

Workup

temperatureto cool to rt
filtrationfiltered through Celite
concentrationThe filtrate is partially concentrated
extractionextracted with EtOAc
washThe organic phase is washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue is purified by silica gel column chromatography (CH2Cl2/NH3 (2 N in MeOH), 95:5)

Sources & evidence

ORD record: ord-06d6aac452524758a13f7cb39adab648
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030311B2

Reaction notes

Loading…