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Reduction of esters and amides

4 real reactions from the literature, on amides, acid chlorides and cyclic anhydrides. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Ester / amide reduction: N-methyldodecanamide with LiAlH4, ether; Δ gives N-methyl-1-dodecanamine (the reduced product).

    Ester / amide reductionOrg. Synth. Coll. Vol. 4, p. 564
  2. Ester / amide reduction: 3,5-dinitrobenzoyl chloride (an acid chloride) with LiAlH(O-t-Bu)3; diglyme, −78 °C gives 3,5-dinitrobenzaldehyde (the reduced product).

    Ester / amide reductionOrg. Synth. Coll. Vol. 6, p. 529
  3. Ester / amide reduction: a cyclic anhydride with LiAlH4; THF, Δ gives the reduced product.

    Ester / amide reductionOrg. Synth. Coll. Vol. 6, p. 482
  4. Ester / amide reduction: N,N-dimethylcyclohexanecarboxamide with LiAlH4; ether, Δ gives N,N-dimethylcyclohexanemethanamine (the reduced product).

    Ester / amide reductionOrg. Synth. Coll. Vol. 4, p. 339