Water → 4-[(Dimethylamino)methyl]-4-methyl-4H-pyrrolo[2,1-c][1,4]-benzoxazine

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Reaction Steps

A solution of the amide of formula 3, N,N,4-trimethyl-4H-pyrrolo-[2,1-c][1,4]benzoxazine-4-carboxamide (3 g), described in Example 15 in 50 ml of ether is added dropwise to a suspension of lithium aluminum hydride (1.5 g) in anhydrous ether (100 ml) over a period of 30 min. The reaction mixture is stirred at room temperature for 16 hr. Decomposition of the mixture with 6 ml of water gives a white precipitate, which is collected on a filter and washed with ether. The filtrate is extracted with 2% aqueous HCl. The extract is rendered basic with a 10% solution of NaOH and extracted with chloroform. The chloroform extract is dried (MgSO4), filtered and evaporated to give the title compound, nmr (DMSO-d6) δ 1.85 (s, 3H), 2.78 (s, 6H).

Provenance & Evidence