2-Aminophenol → 2H-1,4-Benzoxazine

HRID 235279Notes

Reaction equation

HRID 235279 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[C:9](Cl)(=O)[C:10](Cl)=O.C(Cl)Cl>C1(C)C=CC=CC=1>[O:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[CH:10][CH2:9]1

Participants

4

Reactant 2

HCID 58012-AminophenolHCID 21906498HCID 21906498, compound

Product 1

HCID 152462522H-1,4-BenzoxazineYield 110.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2.29 g (21.0 mmol) of o-aminophenol in 25 mL of dry toluene was added portion wise 11 mL of 2N oxalyl chloride/CH2Cl2 (22.0 mmol) solution. The mixture was refluxed for 4 h, cooled to room temperature, filtered and the solid was washed with xylene and water, and dried to leave 3.10 g (90%) of 2a as pale-green solid. The analytical sample was obtained by crystallization from acetone, mp 263°-264° C. (lit, 264°-266° C.; Bernard et al, J. Med. Chem. 28:240 (1985)). 1H NMR (CDCl3 +DMSO-d6), 6.932 (m, 4), 11.970 (m, 1).

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. filtrationfiltered
  3. washthe solid was washed with xylene and water
  4. customdried

Sources & evidence

ORD record
ord-7454c6c48e064a288f620291d5c33deb
Source dataset
uspto-grants-1997_01
Patent number
US05597922

Reaction notes

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