Anthranilic Acid → Bentranil

HRID 559825Notes

Reaction equation

HRID 559825 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:11](Cl)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1>C1COCC1>[C:12]1([C:11]2[O:5][C:4](=[O:6])[C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[N:1]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 1049PyridineHCID 7412Benzoyl chloride

Product 1

HCID 13926Bentranil

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino benzoic acid (10 mmol) in THF was added benzoyl chloride (2.8 g, 20 mmol) followed by pyridine (1.58 g, 20 mmol). The mixture was stirred for 1 h at room temperature. The 2-phenyl-benzo[d][1,3]oxazin-4-one formed was filtered and the residue was washed with water and dried in vacuum desiccator.

Sources & evidence

ORD record
ord-951593031ac54b268bf5bec47952efcc
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Reaction notes

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