N-(4-Chloro-phen-yl)-2-(hydroxy-imino)acetamide

Area of Science:

• Organic Chemistry
• Crystallography
• Chemical Synthesis

Background:

• 5-chloro-isatin is a key precursor in synthesizing various organic compounds.
• Understanding the structural properties of intermediates is crucial for optimizing synthetic pathways.

Purpose of the Study:

• To characterize the structure and intermolecular interactions of a specific chemical intermediate.
• To elucidate the role of this compound in the synthesis of 5-chloro-isatin and its derivatives.

Main Methods:

• X-ray crystallography was employed to determine the molecular and crystal structure.
• Analysis of bond angles, dihedral angles, and hydrogen bonding patterns.

Main Results:

• The compound C(8)H(7)ClN(2)O(2) was identified as an intermediate in 5-chloro-isatin synthesis.
• A dihedral angle of 6.3° was observed between the acetamide plane and the benzene ring.
• Intramolecular C-H⋯O interaction forms a six-membered ring, and intermolecular hydrogen bonds (N-H⋯O, N-H⋯N, O-H⋯O) lead to sheet-like multimers.

Conclusions:

• The structural data provides insights into the compound's stability and reactivity.
• This intermediate is vital for the transformation to 5-chloro-2-indolinone via Wolff-Kishner reduction.
• The observed hydrogen bonding network influences the solid-state packing and properties.