Canadian journal of chemistry

Concerning the mechanism of the Friedländer quinoline synthesis

JM Muchowski, ML Maddox

Index: Muchowski, Joseph M.; Maddox, Michael L. Canadian Journal of Chemistry, 2004 , vol. 82, # 3 p. 461 - 478

Full Text: HTML

Citation Number: 52

Abstract

Detailed experiments regarding the mechanism of the Friedländer synthesis of quinolines from o-aminobenzaldehydes and simple aldehydes or ketones are described. Under the basic or acidic conditions commonly used in this reaction, it is concluded that the first step involves a slow intermolecular aldol condensation of the aldehyde or ketone with the o- aminobenzaldehyde. The aldol adduct 5 generated in this manner then undergoes very ...

 Related Synthetic Route
2-Nitrobenzaldehyde Structure

552-89-6

2-Nitrobenzaldehyde

~%

2,3-Dimethylquinoline Structure

1721-89-7

2,3-Dimethylqui...

Formylaniline Structure

529-23-7

Formylaniline

2-Butanone Structure

78-93-3

2-Butanone

~47%

2,3-Dimethylquinoline Structure

1721-89-7

2,3-Dimethylqui...

2-ethylquinoline Structure

1613-34-9

2-ethylquinoline

4-(2-aminophenyl)-3-methyl-(3E)-buten-2-one Structure

698379-40-7

4-(2-aminopheny...

~%

2,3-Dimethylquinoline Structure

1721-89-7

2,3-Dimethylqui...

4-(2-nitrophenyl)-3-methyl-(3E)-buten-2-one Structure

698380-19-7

4-(2-nitropheny...

~%

2,3-Dimethylquinoline Structure

1721-89-7

2,3-Dimethylqui...

Heptanal Structure

111-71-7

Heptanal

Formylaniline Structure

529-23-7

Formylaniline

~%

3-pentylquinoline Structure

17692-04-5

3-pentylquinoline

2-Nitrobenzaldehyde Structure

552-89-6

2-Nitrobenzaldehyde

~%

3-pentylquinoline Structure

17692-04-5

3-pentylquinoline

2-Nitrobenzaldehyde Structure

552-89-6

2-Nitrobenzaldehyde

~%

Quinoline, 3-phenyl- Structure

1666-96-2

Quinoline, 3-phenyl-

Pentan-2-one Structure

107-87-9

Pentan-2-one

Formylaniline Structure

529-23-7

Formylaniline

~20%

2-propylquinoline Structure

1613-32-7

2-propylquinoline

2-methyl-3-ethylquinoline Structure

57044-36-7

2-methyl-3-ethy...

2-Nitrobenzaldehyde Structure

552-89-6

2-Nitrobenzaldehyde

~%

2-propylquinoline Structure

1613-32-7

2-propylquinoline

Formylaniline Structure

529-23-7

Formylaniline

2-Butanone Structure

78-93-3

2-Butanone

~29%

2,3-Dimethylquinoline Structure

1721-89-7

2,3-Dimethylqui...

2-ethylquinoline Structure

1613-34-9

2-ethylquinoline

2-Nitrobenzaldehyde Structure

552-89-6

2-Nitrobenzaldehyde

~%

3-benzylquinoline Structure

37045-16-2

3-benzylquinoline

3-Phenylpropanal Structure

104-53-0

3-Phenylpropanal

Formylaniline Structure

529-23-7

Formylaniline

~%

3-benzylquinoline Structure

37045-16-2

3-benzylquinoline

2-Nitrobenzaldehyde Structure

552-89-6

2-Nitrobenzaldehyde

~%

2-isobutylquinoline Structure

93-19-6

2-isobutylquinoline

N/A Structure

17418-09-6

N/A

~64%

Quinaldine Structure

91-63-4

Quinaldine

Quinoline, 2-methyl-,1-oxide Structure

1076-28-4

Quinoline, 2-me...

2-Nitrobenzaldehyde Structure

552-89-6

2-Nitrobenzaldehyde

~%

2-ethylquinoline Structure

1613-34-9

2-ethylquinoline

Hept-1-yne Structure

628-71-7

Hept-1-yne

Formylaniline Structure

529-23-7

Formylaniline

~1%

3-(n-butyl)-2-methylquinoline Structure

104361-52-6

3-(n-butyl)-2-m...

2-pentylquinoline Structure

93005-16-4

2-pentylquinoline

2-Nitrobenzaldehyde Structure

552-89-6

2-Nitrobenzaldehyde

~%

2-pentylquinoline Structure

93005-16-4

2-pentylquinoline


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