Chloroacetyl chloride → 6-Nitro-2H-1,4-benzoxazin-3(4H)-one

HRID 417917Notes

Reaction equation

HRID 417917 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].C(N(CC)CC)C.Cl[CH2:20][C:21](Cl)=[O:22].[H-].[Na+]>C1COCC1>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:11][CH2:20][C:21](=[O:22])[NH:1][C:2]=2[CH:7]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 24758Sodium hydrideHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 27636836-Nitro-2H-1,4-benzoxazin-3(4H)-oneYield 39.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using 2-amino-4-nitrophenol (10 g, 65 mmol), triethylamine (11.7 mL, 84 mmol) and chloroacetyl chloride (5.4 mL, 68 mmol) in THF (150 mL) followed by sodium hydride (5.2 g of a 60% suspension in oil, 130 mmol) to yield the title compound as a grey solid (5 g, 33%). δH (DMSO-d6) 4.78 (2H, s), 7.15 (1H, d, J 8.9 Hz), 7.74 (1H, d, J 2.4 Hz), 7.84 (1H, dd, J 8.9, 2.6 Hz), 11.09 (1H, s).

Sources & evidence

ORD record
ord-dfb598a84ae649d893eb266fa0f60981
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

Loading…