77472-71-0

Basic information

• Product Name: 2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide
• Synonyms: 2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide
• CAS NO: 77472-71-0
• Molecular Formula: C12H15N3O2
• Molecular Weight: 233.27
• EINECS: 204-259-2
• Mol File: 77472-71-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 154-155 °C
• Boiling Point: 529.4±50.0 °C(Predicted)
• Density: 1.243±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide(77472-71-0)
• EPA Substance Registry System: 2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide(77472-71-0)

Safety Data

• Hazardous Substances Data: 77472-71-0(Hazardous Substances Data)

Usage

Uses

2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide is mainly used as pharmaceutical intermediates.

Synthetic route

2-oxo-4-phenyl-1-pyrrolidineacetic acid, ethyl ester (70291-40-6) → 2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide (77472-71-0)

Conditions	Yield
With hydrazine hydrate at 0 - 20℃; for 20h;	78%
With hydrazine hydrate In ethanol for 8h; Heating;	67%

4-phenylpyrrolidin-2-one (1198-97-6) → 2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide (77472-71-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) dioxane, 90 deg C, 1 h, 2.) 125 deg C, 5 h 2: 67 percent / hydrazine hydrate / ethanol / 8 h / Heating View Scheme

2-oxo-4-phenylpyrrolidine-3-carboxylic acid (77519-55-2) → 2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide (77472-71-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 58 percent / 0.5 h / 190 °C 2: 1.) NaH / 1.) dioxane, 90 deg C, 1 h, 2.) 125 deg C, 5 h 3: 67 percent / hydrazine hydrate / ethanol / 8 h / Heating View Scheme

3-methoxycarbonyl-4-phenyl-2-pyrrolidone (55790-17-5) → 2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide (77472-71-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 89.6 percent / 10percent aq. KOH / 5 h / Heating 2: 58 percent / 0.5 h / 190 °C 3: 1.) NaH / 1.) dioxane, 90 deg C, 1 h, 2.) 125 deg C, 5 h 4: 67 percent / hydrazine hydrate / ethanol / 8 h / Heating View Scheme

4-chlorobenzaldehyde (104-88-1) + 2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide (77472-71-0) → N'-[(E)-(4-chlorophenyl)methylidene]-2-(4-phenyl-2-oxopyrrolidin-1-yl)acetohydrazide

Conditions	Yield
In ethanol Reflux;	89%

2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide (77472-71-0) + acetone (67-64-1) → 2-(4-phenyl-2-oxopyrrolidin-1-yl)-N'-isopropylideneacetohydrazide

Conditions	Yield
for 1h; Reflux;	85%

benzaldehyde (100-52-7) + 2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide (77472-71-0) → 2-(4-phenyl-2-oxopyrrolidin-1-yl)-N'-[(E)-phenyl methylidene]acetohydrazide

Conditions	Yield
In ethanol Reflux;	81%

4-methoxy-benzaldehyde (123-11-5) + 2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide (77472-71-0) → N'-[(E)-(4-methoxyphenyl)methylidene]-2-(4-phenyl-2-oxopyrrolidin-1-yl)acetohydrazide

Conditions	Yield
In ethanol Reflux;	71%

2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide (77472-71-0) + acetophenone (98-86-2) → 2-(4-phenyl-2-oxopyrrolidin-1-yl)-N'-[(1E)-1-phenyl ethylidene]acetohydrazide

Conditions	Yield
In ethanol for 3h; Reflux;	69%

3-pyridinecarboxaldehyde (500-22-1) + 2-Oxo-4-phenylpyrrolidine-1-acetic acid hydrazide (77472-71-0) → 2-(4-phenyl-2-oxopyrrolidin-1-yl)-N'-[(E)-(pyridin-3-yl)methylidene]acetohydrazide

Conditions	Yield
In ethanol Reflux;	62%

Upstream product

• 55790-17-5 3-methoxycarbonyl-4-phenyl-2-pyrrolidone 
• 77519-55-2 2-oxo-4-phenylpyrrolidine-3-carboxylic acid 
• 1198-97-6 4-phenylpyrrolidin-2-one 
• 70291-40-6 2-oxo-4-phenyl-1-pyrrolidineacetic acid, ethyl ester 

Relevant articles and documents

2-[4-(Het)aryl-2-oxopyrrolidin-1-yl]acetohydrazides: synthesis, structures, and reactions with carbonyl compounds

2-[4-(Het)aryl-2-oxopyrrolidin-1-yl]acetohydrazides, structural analogs of piracetam, were synthesized by the condensation of 2-[4-(het)aryl-2-oxopyrrolidin-1-yl]acetates with hydrazine hydrate and phenylhydrazine. New [N′-alkyl(hetaryl)idene]-4-(het)aryl-2-oxopyrrolidin-1-ylacetohydrazides were synthesized by the reaction of 2-[4-(het)aryl-2-oxopyrrolidin-1-yl]-acetohydrazides with aromatic aldehydes, acetone, and acetophenone.