draw the entire synthesis of ( 8 - Hydroxy-2-isopropyl-3,4-dihydroisoquinolin-1 (2H)-one) as mentioned in the picture (with arrows, lone pairs, substitution and elimination)1. Start with benzaldehyde:Benzaldehyde + Ethyl acetoacetate → ChalconeThis reaction is a Claisen-Schmidt condensation. The Chalconeobtained has a benzene ring and a three-carbon side chain.2. Next, perform a Pictet-Spengler reaction:Chalcone + Ethylamine → Isoquinoline derivativeThis reaction forms the isoquinoline ring system.3. Hydrogenate the isoquinoline derivative:Isoquinoline derivative + H2/Pd-C3,4-dihydroisoquinolineThis step reduces the double bond in the isoquinoline ring.4. Oxidize the 3,4-dihydroisoquinoline to obtain the desiredproduct:3,4-dihydroisoquinoline + KMnO4/H2O8-Hydroxy-2-isopropyl-3,4-dihydroisoquinolin-1(2H)-one

The objective of this question is to plan a multistep synthesis pathway starting from a given…

Answered: draw the entire synthesis of…

draw the entire synthesis of (8-Hydroxy-2-isopropyl-3,4-dihydroisoquinolin-1 (2H)-one) as mentioned in the picture ( with arrows, lone pairs, substitution and elimination)

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 35CTQ

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Question

draw the entire synthesis of ( 8 - Hydroxy-2-isopropyl-3,4-dihydroisoquinolin-1 (2H)-one) as mentioned in the picture (
with arrows, lone pairs, substitution and elimination)
1. Start with benzaldehyde:
Benzaldehyde + Ethyl acetoacetate → Chalcone
This reaction is a Claisen-Schmidt condensation. The Chalcone
obtained has a benzene ring and a three-carbon side chain.
2. Next, perform a Pictet-Spengler reaction:
Chalcone + Ethylamine → Isoquinoline derivative
This reaction forms the isoquinoline ring system.
3. Hydrogenate the isoquinoline derivative:
Isoquinoline derivative + H2/Pd-C
3,4-dihydroisoquinoline
This step reduces the double bond in the isoquinoline ring.
4. Oxidize the 3,4-dihydroisoquinoline to obtain the desired
product:
3,4-dihydroisoquinoline + KMnO4/H2O8-Hydroxy-2-
isopropyl-3,4-dihydroisoquinolin-1(2H)-one

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