Reaction #1563895

Reaction equation

2,2,-dimethyl-1,4-dihydro-2H-benzo[1,3]oxazine

THF

LiAlH4

THF

→

2-isopropylaminophenylmethanol

Yield 95.0%

Conditions

Workup

1. 1
   OtherThe reaction was quenched by slow portionwise addition of Na2SO4.10H2O (110 g), over a period of 1.5 h, at 0° C
2. 2
   Filtrationfiltered
3. 3
   Washthe solid salts were washed thoroughly with THF
4. 4
   ConcentrationThe filtrate was concentrated under reduced pressure

Procedure

A solution of 2,2,-dimethyl-1,4-dihydro-2H-benzo[1,3]oxazine (125 g, 0.77 mol) in THF (1 L) was filtered through a scintillation funnel and then added dropwise via an addition funnel, over a period of 2.5 h, to a stirred solution of 1.0 M LiAlH4 in THF (800 mL) at 0° C. The reaction was quenched by slow portionwise addition of Na2SO4.10H2O (110 g), over a period of 1.5 h, at 0° C. The reaction mixture was stirred overnight, filtered and the solid salts were washed thoroughly with THF. The filtrate was concentrated under reduced pressure to yield 2-isopropylaminophenylmethanol (120 g, 95%) as a yellow oil. 1H NMR (CDCl3; 300 MHz): 1.24 (d, 6H, CH(CH3)2), 3.15 (bs, 1H, OH), 3.61 (sept, 1H, CH(CH3)2), 4.57 (s, 2H, CH2), 6.59 (t, 1H, ArH), 6.65 (d, 1H, ArH), 6.99 (d, 1H, ArH), 7.15 (t, 1H, ArH).

Source