Hydrochloric Acid → 6-ethyl-N,N-dimethyl-2-methoxy-benzamide

HRID 1729169Notes

Reaction equation

[CH3:1][N:2]([CH3:13])[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11].CN(C)[CH2:16][CH2:17]N(C)C.C([Li])(CC)C.C(Br)C.Cl>C1CCCCC1.CCC(C)C.O.O1CCCC1>[CH2:16]([C:9]1[C:4]([C:3]([N:2]([CH3:1])[CH3:13])=[O:12])=[C:5]([O:10][CH3:11])[CH:6]=[CH:7][CH:8]=1)[CH3:17]

Participants

Conditions

Temperature: -70 °C

Procedure

39.5 g of N,N-dimethyl-2-methoxy-benzamide and 28.5 ml of tetramethylethylenediamine are introduced into 190 ml of absolute tetrahydrofuran and the mixture is lithiated at -70° C. with 150 ml of a 1.4-molar sec-butyllithium solution in cyclohexane/isopentane. After subsequently stirring at -70° C. for 45 minutes, 25.6 ml of ethyl bromide are added dropwise within 25 minutes and the reaction mixture is then allowed to warm slowly to room temperature. Water is then added and the mixture is adjusted to pH 2 with hydrochloric acid and extracted twice with diethyl ether. The residue is purified on silica gel using ethyl acetate/n-hexane (4:6) to yield 6-ethyl-N,N-dimethyl-2-methoxy-benzamide in the form of a colourless oil, 1H-NMR (CDCl3): 3 82 ppm (m), 3.40 ppm (m) and 3.12 ppm (2q, N(CH2CH3)2), 2.56 ppm (m, CH2CH3).

Workup

temperatureto warm slowly to room temperature
extractionextracted twice with diethyl ether
customThe residue is purified on silica gel

Sources & evidence

ORD record: ord-61c1765f57474a01875be7f5664d6dd8
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05332717

Reaction notes

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