Water → N-methyl-2,6-dimethoxy-4-methylaniline

HRID 2921Notes

Reaction equation

[CH:1]([NH:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([CH3:12])=[CH:6][C:5]=1[O:13][CH3:14])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][NH:3][C:4]1[C:5]([O:13][CH3:14])=[CH:6][C:7]([CH3:12])=[CH:8][C:9]=1[O:10][CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

6 g of N-formyl-2,6-dimethoxy-4-methylaniline are suspended in 100 ml of tetrahydrofuran and then 33 ml of a 1M solution of lithium aluminium hydride in tetrahydrofuran are added dropwise under an inert atmosphere. The reaction mixture become homogeneous. The reaction mixture is left at room temperature for 2 hours and then, after cooling to 0° C., 1 ml of water, then 1 ml of a 15% aqueous sodium hydroxide solution and then 3 ml of water are successively added dropwise to the reaction mixture. The whole mixture is diluted with 100 ml of ethyl acetate and the precipitate is filtered. The filtrate, evaporated to dryness, leaves an oily residue which is purified by flash chromatography on a column of silica gel, eluent: toluene/ethyl acetate 8/2 (v/v) in order to obtain N-methyl-2,6-dimethoxy-4-methylaniline in the form of an oil, Yield: 85%.

Workup

filtrationthe precipitate is filtered
customThe filtrate, evaporated to dryness
customleaves an oily residue which
customis purified by flash chromatography on a column of silica gel, eluent

Sources & evidence

ORD record: ord-50d4e1528b5f4200af2c175551ee6a2e
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05731340

Reaction notes

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