6-Chloro-2H-1,4-benzoxazin-3(4H)-one → 6-Chloro-3,4-dihydro-2H-1,4-benzoxazine

HRID 417922Notes

Reaction equation

HRID 417922 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=O)[NH:7][C:6]=2[CH:12]=1.B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:12]=1

Participants

4

Reactant 2

HCID 3092596-Chloro-2H-1,4-benzoxazin-3(4H)-oneHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 125105446-Chloro-3,4-dihydro-2H-1,4-benzoxazineYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Using 6-chloro-4H-benzo[1,4]oxazin-3-one (0.6 g, 3.3 mmol) and borane-THF (16.4 mL of a 1M solution in THF, 16.4 mmol) in THF (15 mL) to yield the title compound as a clear oil (0.16 g, 55%). δH (CDCl3) 3.35-3.47 (2H, m), 3.81 (1H, br s), 4.17-4.29 (2H, m), 6.54-6.62 (2H, m), 6.64-6.72 (1H, m).

Sources & evidence

ORD record
ord-2cea16720934486ebd79bf7b8de20817
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

Loading…