7-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-one → 7-Nitro-3,4-dihydro-2H-1,4-benzoxazine

HRID 990924Notes

Reaction equation

HRID 990924 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[NH:8][C:9](=O)[CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].CSC.B>>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[NH:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 27638307-nitro-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 184161517-Nitro-3,4-dihydro-2H-1,4-benzoxazineYield 102.1%

Procedure

This compound was prepared by General Method 2 from 7-nitro-2H-1,4-benzoxazin-3(4H)-one (2.0 g, 10 mmol) and borane dimethylsulfide (2.0 M in THF, 24 mL, 48 mmol) and purified on silica gel (20:1 CH2Cl2;MeOH) to afford 1.84 g (98%) of 3,4-dihydro-7-nitro-2H-1,4-benzoxazine, an orange solid. Data for 3,4-dihydro-7-nitro-2H-1,4-benzoxazine: Rf 0.76 (11.5:1 CH2Cl2:MeOH); 1H NMR (400 MHz, CDCl3) δ 7.74 (dd, 1H, J=8.7, 2.5), 7.69 (d, 1H, J=2.5), 6.52 (d, 1H, J=8.7), 4.56 (br s, 1H), 4.26 (t, 2H, J=4.4), 3.54 (td, 2H, J=4.4, 2.5)

Workup

  1. custompurified on silica gel (20:1 CH2Cl2;MeOH)

Sources & evidence

ORD record
ord-1e1028dde1404b639c69ebfbe5cc27ef
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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