2-Amino-4-methylphenol → 2,3-dihydroxy-5-(6-methyl-2-oxo-2H-1,4-benzoxazin-3-yl)benzonitrile

HRID 1781866Notes

Reaction equation

HRID 1781866 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:11](=O)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[C:7]([OH:10])[C:8]=1[OH:9])#[N:2].[NH2:17][C:18]1C(O)=[CH:22][CH:21]=[C:20]([CH3:25])[CH:19]=1>CN(C)C=O.O>[OH:9][C:8]1[C:7]([OH:10])=[CH:6][C:5]([C:11]2[C:12](=[O:13])[O:14][C:15]3[CH:22]=[CH:21][C:20]([CH3:25])=[CH:19][C:18]=3[N:17]=2)=[CH:4][C:3]=1[C:1]#[N:2]

Participants

5

Reactant 2

HCID 72642-Amino-4-methylphenolHCID 14451002Methyl (3-cyano-4,5-dihydroxyphenyl)glyoxylate

Product 1

HCID 1356653052,3-dihydroxy-5-(6-methyl-2-oxo-2H-1,4-benzoxazin-3-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.075 g of methyl (3-cyano-4,5-dihydroxyphenyl)glyoxylate and 0.60 g of 2-amino-p-cresol are stirred at 120° for 70 minutes in 2 ml of dimethylformamide. The mixture is subsequently cooled to room temperature and diluted with 15 ml of water: The precipitate is filtered and dried in a water-jet vacuum at 80° for 6 hours. After recrystallization from acetonitrile there is obtained 2,3-dihydroxy-5-(6-methyl-2-oxo-2H-1,4-benzoxazin-3-yl)-benzonitrile of m.p. 278°-280°.

Workup

  1. filtrationThe precipitate is filtered
  2. dry with materialdried in a water-jet vacuum at 80° for 6 hours
  3. customAfter recrystallization from acetonitrile

Sources & evidence

ORD record
ord-0548a9daa64744ec8755fee0bf4c32c0
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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