Borane;tetrahydrofuran → 7-Chloro-3,4-dihydro-2H-1,4-benzoxazine

HRID 417924Notes

Reaction equation

HRID 417924 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=O)[CH2:8][O:9][C:4]=2[CH:3]=1.B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 118300867-Chloro-2H-1,4-benzoxazin

Product 1

HCID 136432417-Chloro-3,4-dihydro-2H-1,4-benzoxazineYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Using 7-chloro-4H-benzo[1,4]oxazin-3-one (2.3 g, 13.5 mmol) and borane-THF (40 mL of a 1M solution in THF, 40 mmol) in THF (40 mL) to yield the title compound as a cream solid (2.2 g, 96%). δH (CDCl3) 3.34-3.40 (2H, m), 4.16-4.28 (2H, m), 6.51-6.55 (1H, m), 6.59 (1H, d, J 2.4 Hz), 6.68 (1H, dd, J 8.1, 0.4 Hz). LCMS (ES+) 170 (M+H)+.

Sources & evidence

ORD record
ord-fb4857b93b88418da65f030b12f25cac
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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