Acetic Acid → HCID 20258679, compound

HRID 1583493Notes

Reaction equation

HRID 1583493 reaction equation
[F:1][CH:2]([C:8](=O)C1C=CC=CC=1)[C:3](OCC)=[O:4].[C:16]1([NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH2:22].C(O)(=O)C>C(O)C>[F:1][C:2]1[C:3](=[O:4])[N:23]=[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]2=[N:22][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7243O-PhenylenediamineHCID 12646284Ethyl 2-fluoro-3-oxo-3-phenylpropanoate

Product 1

HCID 20258679HCID 20258679, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Refluxing of ethyl α-fluorobenzoylacetate (2.25 g, 10 mmol) with o-phenylenediamine (10 mmol) in the mixture of acetic acid and ethanol (25%) for 5 h gave 3-fluoro-1,5-benzodiazepin-2-one derivatives in good yields as follows. ##STR17## wherein X=H, 4-Me, 4-Cl or NO2. It is clear that the first step of this reaction is condensation of carbonyl ketone and amine by losing water and second step is cyclization of their ester with another amine by losing ethanol. When used p-CH3 or p-Cl o-phenylenediamine, these were condensed with α-fluorobenzoylacetate,

Sources & evidence

ORD record
ord-06e09e79dfb146ff82004ef9b9b3ead1
Source dataset
uspto-grants-1985_11
Patent number
US04552694

Reaction notes

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