Diisopropylethylamine → Benzamide, o-methoxy-N-methyl-

HRID 235531Notes

Reaction equation

HRID 235531 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH:12]([N:15](C(C)C)CC)(C)C.Cl.CN>O1CCCC1>[CH3:12][NH:15][C:1](=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 889692-Methoxybenzoyl chlorideHCID 6364545Methylamine hydrochloride

Product 1

HCID 76940Benzamide, o-methoxy-N-methyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine o-anisoyl chloride (2-methoxybenzoyl chloride) (2.9 g, 17.0 mmol) and tetrahydrofuran (170 mL) and cool to 0° C. Add diisopropylethylamine (5.92 mL, 34 mmol). Add methylamine hydrochloride (1.26 g, 18.7 mmol). Allow to stir for 1 hour and concentrate in vacuo. Chromatograph on silica gel eluting sequentially with 50% ethyl acetate/hexane to give N-methyl-2-methoxybenzamide: TLC Rf =0.45 (silica gel, 50% ethyl acetate/hexane).

Workup

  1. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-a40c12effd3d42bcb1f960513c10917d
Source dataset
uspto-grants-1997_01
Patent number
US05597845

Reaction notes

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