Chloroacetyl chloride → 2H-1,4-Benzoxazine-8-carboxylic acid, 3,4-dihydro-3-oxo-, ethyl ester

HRID 1533798Notes

Reaction equation

[NH2:1][C:2]1[C:3]([OH:13])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(=O)([O-])O.[Na+].Cl[CH2:20][C:21](Cl)=[O:22]>[Br-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C(Cl)(Cl)Cl>[O:13]1[C:3]2[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:10][CH:11]=[CH:12][C:2]=2[NH:1][C:21](=[O:22])[CH2:20]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 3-amino-2-hydroxybenzoate (500 mg), sodium hydrogen carbonate (927 mg) and benzyltributylammonium bromide (983 mg) in chloroform (10 ml) was added dropwise chloroacetyl chloride (374 mg) in chloroform (3 ml) under ice bath cooling. The reaction mixture was stirred at ambient temperature for 1 hour and at 60° C. for 2 hours. To the reaction mixture was added dropwise chloroacetyl chloride (312 mg) in chloroform (3 ml) under ice bath cooling and stirred at 60° C. for 2 hours. After the reaction mixture was concentrated in vacuo, the residue was diluted with chloroform and saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and washed with brine. The solution was dried over magnesium sulfate and concentrated in vacuo to give ethyl 2H-1,4-benzoxazin-3-one-8-carboxylate (460 mg).

Workup

temperaturecooling
temperaturecooling
stirringstirred at 60° C. for 2 hours
concentrationAfter the reaction mixture was concentrated in vacuo
additionthe residue was diluted with chloroform and saturated sodium hydrogen carbonate aqueous solution
customThe organic layer was separated
washwashed with brine
dry with materialThe solution was dried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-58738d5577134f4a8bc37bfc5fc7d86a
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06207693B1

Reaction notes

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