6-Amino-2H-1,4-benzoxazin-3(4H)-one

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6-Amino-2H-1,4-benzoxazin-3(4H)-one Basic information
Product Name:6-Amino-2H-1,4-benzoxazin-3(4H)-one
Synonyms:6-AMINO-4H-BENZO[1,4]OXAZIN-3-ONE;2H-1,4-benzoxazin-3(4H)-one, 6-amino-;6-Amino-2H-1,4-benzoxin-3(4H)-one;6-amino-2H-1,4-benzoxazin-3(4H)-one(SALTDATA: FREE);6-Amino-3,4-dihydro-3-oxo-2H-1,4-benzoxazine;6-Amino-3-oxo-3,4-dihydrobenzo[1,4]oxazine;6-AMino-3,4-dihydro-2H-1,4-benzoxazin-3-one;6-amino-2,4-dihydro-1,4-benzoxazin-3-one
CAS:89976-75-0
MF:C8H8N2O2
MW:164.16
EINECS:
Product Categories:
Mol File:89976-75-0.mol
6-Amino-2H-1,4-benzoxazin-3(4H)-one Structure
6-Amino-2H-1,4-benzoxazin-3(4H)-one Chemical Properties
Melting point 266-268°C
density 1.344
storage temp. 2-8°C
form solid
color Pale brown
InChI1S/C8H8N2O2/c9-5-1-2-7-6(3-5)10-8(11)4-12-7/h1-3H,4,9H2,(H,10,11)
InChIKeyGEPGYMHEMLZMBC-UHFFFAOYSA-N
SMILESNc1ccc2OCC(=O)Nc2c1
Safety Information
Hazard Codes Xn
Risk Statements 36/37/38-52-22
Safety Statements 26-36/37/39-24/25
WGK Germany 3
HazardClass IRRITANT
HS Code 29349990
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
6-Amino-2H-1,4-benzoxazin-3(4H)-one Usage And Synthesis
Synthesis
6-NITRO-2H-1,4-BENZOXAZIN-3(4H)-ONE

81721-87-1

6-AMINO-2H-1,4-BENZOXAZIN-3(4H)-ONE

89976-75-0

General procedure for the synthesis of 6-amino-2H-1,4-benzomorpholin-3(4H)-one from 6-nitro-2H-1,4-benzoxazin-3(4H)-one: to a solution of 6-nitro-2H-1,4-benzoxazin-3(4H)-one (2.97 g, 15.00 mmol) in methanol (50 mL) was added 10% palladium/carbon catalyst (0.30 g). The reaction mixture was stirred under hydrogen atmosphere for 16 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to afford 6-amino-2H-1,4-benzomorpholin-3(4H)-one (2.36 g, 95% yield) as a brown solid. Mass spectrometry (MS) analysis showed a molecular ion peak of 165 (M + H).

References[1] ChemCatChem, 2014, vol. 6, # 11, p. 3153 - 3159
[2] Patent: WO2018/19252, 2018, A1. Location in patent: Page/Page column 37
[3] ChemSusChem, 2017, vol. 10, # 15, p. 3035 - 3039
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 71 - 90
[5] Patent: US2009/298819, 2009, A1. Location in patent: Page/Page column 16; 22
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