[CH:1]([NH:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:5]=1[CH2:6][OH:7])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:12][C:8]1[C:5]([CH2:6][OH:7])=[C:4]([NH:3][CH3:1])[CH:11]=[CH:10][CH:9]=1A solution of 2-formamido-6-methylbenzyl alcohol (1.9 g) in tetrahydrofuran (26 ml) was added dropwise to a suspension of lithium aluminum hydride (0.873 g) in tetrahydrofuran (17 ml) at room temperature over a period of 10 minutes. After being refluxed for 4.5 hours, the excess reagent was decomposed with a small amount of water and the resulting precipitates were filtered off by suction. The filtrate was evaporated in vacuo and the residue was recrystallized from carbon tetrachloride to give 6-methyl-2-methylaminobenzyl alcohol (0.86 g).
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