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Ketone/aldehyde + amine (H2N—Z)
Imine (C=N—Z)
Can reduce imine to form amine
Primary amine + alkyl halide
secondary amine
Excess ammonia (10 moles) + alkyl halide
primary amine
ammonia/primary/secondary amine + acid chloride
Amide (nucleophilic acyl substitution)
(can reduce amide using LiALH4 to form amine)
primary/secondary amine + sulfonyl chloride
sulfonamide
Amine + carboxylic acid
amide
Nitrile + LiAlH4
primary amine
Nitrile + H2/metal catalyst
primary amine
NO2 + Sn, HCl, NaOH
NH2 (converts nitro group to amino group)