Pfitzinger reaction

Pfitzinger reaction
Named after	Wilhelm Pfitzinger
Reaction type	ring-condensation
Reaction
	ketone or aldehyde
	+; isatin
	+; potassium hydroxide
	↓
	quinoline-4-carboxylic acid
	+; water
Conditions
Typical solvents	protic
Identifiers
RSC ontology ID	RXNO:0000109

The Pfitzinger reaction (also known as the Pfitzinger-Borsche reaction) is the chemical reaction of isatin with base and a carbonyl compound to yield substituted quinoline-4-carboxylic acids.^[1]^[2]

Several reviews have been published.^[3]^[4]^[5]

Reaction mechanism

The reaction of isatin with a base such as potassium hydroxide hydrolyses the amide bond to give the keto-acid 2. This intermediate can be isolated, but is typically not. A ketone (or aldehyde) will react with the aniline to give the imine (3) and the enamine (4). The enamine will cyclize and dehydrate to give the desired quinoline (5).

Variations

Halberkann variant

Reaction of N-acyl isatins with base gives 2-hydroxy-quinoline-4-carboxylic acids.^[6]

References

^ Pfitzinger, W. (1886). "Chinolinderivate aus Isatinsäure". J. Prakt. Chem. (in German). 33 (1): 100. doi:10.1002/prac.18850330110.
^ Pfitzinger, W. (1888). "Chinolinderivate aus Isatinsäure". J. Prakt. Chem. (in German). 38 (1): 582–584. doi:10.1002/prac.18880380138.
^ Manske, R. H. (1942). "The Chemistry of Quinolines". Chem. Rev. 30 (1): 113–144. doi:10.1021/cr60095a006.
^ Bergstrom, F. W. (1944). "Heterocyclic Nitrogen Compounds. Part IIA. Hexacyclic Compounds: Pyridine, Quinoline, and Isoquinoline". Chem. Rev. 35 (2): 77–277. doi:10.1021/cr60111a001.
^ Shvekhgeimer, M. G.-A. (2004). "The Pfitzinger Reaction". Chem. Heterocycl. Compd. 40 (3): 257–294. doi:10.1023/B:COHC.0000028623.41308.e5. S2CID 97698676.)
^ Halberkann, J. (1921). "Abkömmlinge der Chininsäure". Chem. Ber. (in German). 54 (11): 3090–3107. doi:10.1002/cber.19210541118.

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[1] Pfitzinger, W. (1886). "Chinolinderivate aus Isatinsäure". J. Prakt. Chem. (in German). 33 (1): 100. doi:10.1002/prac.18850330110.

[2] Pfitzinger, W. (1888). "Chinolinderivate aus Isatinsäure". J. Prakt. Chem. (in German). 38 (1): 582–584. doi:10.1002/prac.18880380138.

[Manske1942-3] Manske, R. H. (1942). "The Chemistry of Quinolines". Chem. Rev. 30 (1): 113–144. doi:10.1021/cr60095a006.

[4] Bergstrom, F. W. (1944). "Heterocyclic Nitrogen Compounds. Part IIA. Hexacyclic Compounds: Pyridine, Quinoline, and Isoquinoline". Chem. Rev. 35 (2): 77–277. doi:10.1021/cr60111a001.

[5] Shvekhgeimer, M. G.-A. (2004). "The Pfitzinger Reaction". Chem. Heterocycl. Compd. 40 (3): 257–294. doi:10.1023/B:COHC.0000028623.41308.e5. S2CID 97698676.)

[6] Halberkann, J. (1921). "Abkömmlinge der Chininsäure". Chem. Ber. (in German). 54 (11): 3090–3107. doi:10.1002/cber.19210541118.

[1]

[2]

[3]

[4]

[5]

[6]

Reaction mechanism

Variations

Halberkann variant

See also

References