N-methylhydroxylamine hydrochloride → 5,6,7,8-Tetrahydro-7-(N-hydroxymethylamino)quinoline

Reaction equation

[N:1]1[C:10]2[CH:9]=[CH:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[CH3:12][NH:13]O.C(=O)(O)[O-:16].[Na+]>CO>[OH:16][CH2:12][NH:13][CH:8]1[CH2:9][C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7]1

Participants

Procedure

A solution of 5,6-dihydroquinoline (9.17g, 0.07 mmol) in methanol (10 ml) at 0° was treated portionwise with N-methylhydroxylamine hydrochloride (11.5 g, 0.138 mmol), stirred for 2 h, poured into saturated aqueous sodium bicarbonate (250 ml), and extracted with chloroform (3×150 ml). The extracts were washed with water (50 ml), dried (MgSO4), and evaporated in vacuo. The residual brown liquid was purified by chromatography (alumina; ether) to give the product (6.45 g) as a colourless oil, which was converted into the amine of Example 2.