3,4-Dimethylaniline → N-(3,4-Dimethyl-phenyl)-2-(5-methyl-pyridin-2-yl)-acetamide

HRID 1094357Notes

Reaction equation

Cl.[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([OH:12])=O)=[N:7][CH:8]=1.[CH3:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[CH3:21])[NH2:17].Cl.CN(C)CCCN=C=NCC>ClCCl>[CH3:13][C:14]1[CH:15]=[C:16]([NH:17][C:10](=[O:12])[CH2:9][C:6]2[CH:5]=[CH:4][C:3]([CH3:2])=[CH:8][N:7]=2)[CH:18]=[CH:19][C:20]=1[CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 400 mg (2.12 mmol) (5-methyl-pyridin-2-yl)-acetic acid hydrochloride (CAS: 848093-05-0) in 7.5 mL dichloromethane were added successively 250 mg (2.02 mmol) 3,4-dimethylaniline and 415.4 mg (2.12 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The mixture was stirred at 0° C. for 45 minutes. The solution was washed with a sat. NaHCO3 solution, NaOH 2N and with water, dried over Na2SO4, filtered and concentrated in vacuo. The crude solid was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 0.40 g (77%) of the title compound as an off-white solid. MS (m/e): 255.2 [M+H]+.

Workup

washThe solution was washed with a sat. NaHCO3 solution, NaOH 2N and with water
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude solid was purified with flash column chromatography on silica eluting with a gradient
customformed from heptane and ethylacetate

Sources & evidence

ORD record: ord-0f885843e9bd4acca932ac9108d7d5c8
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133909B2

Reaction notes

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