2-Aminophenol → 2H-1,4-Benzoxazine-2,3(4H)-dione
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[C:9](Cl)(=[O:13])[C:10](Cl)=[O:11]>ClC1C=CC=CC=1Cl>[O:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:10](=[O:11])[C:9]1=[O:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Ortho-aminophenol (21.8 g) in 200 ml of ortho-dichlorobenzene was added as a slurry to 18.3 ml oxalyl dichloride (1.05 mol eq) in 150 ml ortho-dichlorobenzene at about 100° C. with stirring. After the addition (about 30 min.), the reaction mixture was heated to about 70° C. and then kept at this temperature for approximately 1.5 hours. The reaction mixture was then cooled, filtered and the solid product, 4H-1,4-benzoxazin-2,3-dione was washed with ether to give 27 g., m.p. 265°-268° C.
Workup
- additionAfter the addition (about 30 min.)
- temperatureThe reaction mixture was then cooled
- filtrationfiltered
- washthe solid product, 4H-1,4-benzoxazin-2,3-dione was washed with ether
- customto give 27 g
Sources & evidence
- ORD record
- ord-e32c8dfac3a1472f83cd5ed2f255afef
- Source dataset
- uspto-grants-1981_12
- Patent number
- US04307091
Reaction notes
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