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Chapter 25: PROBLEM 25.14 (page 1012)

Question: Enalapril, a drug used to treat hypertension, is prepared from compounds D and E by reductive amination. What is the structure of enalapril?

Short Answer

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Answer

Step by step solution

01

Reduction of aldehyde to amine

The carbonyl carbon of the aldehyde or ketone is reduced by the attack of an amine group.

The electron pair donated by the amine group is accepted by the electron-deficient C=O.

02

Reduction of imine to amine

Reducing agents such as sodium cyanoborohydride are used to reduce imine to primary, secondary, or tertiary amine.

03

Explanation

The given ketone compound is reduced to amine, as shown below.

Formation of the product enalapril by the reduction of ketone

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Most popular questions from this chapter

Question: What is the structure of an unknown compound with molecular formula C6H15N that gives the following 1H NMR absorptions: 0.9 (singlet, 1 H), 1.10 (triplet, 3 H), 1.15 (singlet, 9 H), and 2.6 (quartet, 2 H) ppm?

Question: Rank the following compounds in order of increasing basicity and explain the order you chose.

Question: Draw the product formed in each reaction.

a.

b.

c.

d.

A chiral amine A having the R configuration undergoes Hofmann elimination to form an alkene B as the major product. B is oxidatively cleaved with ozone, followed by CH3SCH3 , to form CH2=O andCH3CH2CH2CHO .What are the structures of A and B?

Draw the products formed when p-methylaniline ( p-C6H4NH2) is treated with each reagent.

  1. HCl
  2. CH3COCl
  3. CH3CO2O
  4. Excess CH3I
  5. CH32C=O
  6. CH3COCl,AlCl3
  7. CH3CO2H
  8. NaNO2,HCl
  9. Part (b), thenCH3COCl,AlCl3
  10. CH3CHO,NaBH3CN
See all solutions

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