Synthetic Organic Chemistry by Gaman Barat

Author:Gaman Barat [Barat, Gaman]
Language: eng
Format: azw3
Publisher: Green Flag Foundation, Sonasan
Published: 2015-07-27T16:00:00+00:00

H3CO CH2 - OHH3CO

+

CH - OH

conc. H2SO4, C6H5NO2

NO2 skraup synthesisN NO2 CH2 - OH

3-nitro p- anisidine glycerolNO2 Reduction

H3CO

N

NH2

6-methoxy-8-aminoquinoline

(B) Synthesis of 1-diethylamino-4-bromopentane

CH3-CHO CH CH CH3-CH(OH)-C CHHO CH2N(C2H5)2 CH3-CH(OH)-C C-CH2N(C2H5)2

Reduction

CH3-CH(CH2)2N(C2H5)

SOBr2

2 CH3-CH(CH2)3N(C2H5)2 OH Br (B)

(C) Condensation of A and B to give pemaquine.

H3COH3CO

+CH3-CH(CH2)3N(C2H5)2

N BrN

NHCH(CH2)3N(C2H5)2NH2 (B)6-methoxy-8-aminoquinolineCH3(A) Pemaquine

(ii) Primaquine: It is unalkylated amine analogue to pemaquine. It is prepared by condensing 6-methoxy-8-aminoquinoline with 4-bromopentylamine hydrobromide. H3CO

+CH3-CH(CH2)3NH2HBr N Br

NH2

6-methoxy-8-aminoquinoline

H3CO

N

NH-CH(CH2)3NH2 CH3 Primaquine (iii) Pentaquine: It is obtained by the condensing 6-methoxy-8-amino quinoline with 1-chloro-5-isopropyl aminopentane (C). The compound (C) is obtained by the following method;

Al2O3 H2O ; H+

O CH2OH320 0C O OH OHC CH2OH teterahydro furfuryl

alcohol

(CH3)2CHNH2 (CH3)2CHN C CH2OHH2 CH2OH(CH2)4NHCH(CH3)SOCl2 2

CH2Cl(CH2)4NHCH(CH3)2 1-chloro-5-isopropyl amino pentane H3CO

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