Methanol → 6-Hydroxy-2H-1,4-benzoxazin-3(4H)-one

HRID 34697Notes

Reaction equation

HRID 34697 reaction equation
C[O-].[Na+].CO.Cl[CH2:7][C:8]([NH:10][C:11]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:12]=1[OH:13])=[O:9].O>CN(C)C=O>[OH:18][C:16]1[CH:15]=[CH:14][C:12]2[O:13][CH2:7][C:8](=[O:9])[NH:10][C:11]=2[CH:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 10942334Sodium MethoxideHCID 212986772-Chloro-N-(2,5-dihydroxy-phenyl)-acetamide

Product 1

HCID 113786896-Hydroxy-2H-1,4-benzoxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

30% sodium methoxide in methanol (18.4 g, 0.075 mole) was added under stirring to the 2-(α-chloroacetamido)-hydroquinone (13.4 g, 0.075 mole) in dimethylformamide (DMF 10 ml). The resulting solution was poured into water (150 ml) and the separated solid was Coupler (1) (9 g, 73%).

Sources & evidence

ORD record
ord-b52cafd4e953474a8c6bb7c03f548191
Source dataset
uspto-grants-1988_08
Patent number
US04762925

Reaction notes

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