amine reactions

After Gabriel synthesis NH2NH2

Releases primary amine (r-nh2) from the big ah molecule phthalimide

LiAlH4/H2O on RCN (nitrile)

Primary amine (r-nh2)

H2/Pd/pt on RCN (nitrile)

Primary amine

LiAlH₄/H₂O

Azide (RN₃)

Primary amine

H₂/Ni (or Pd/Pt)

Nitro (ArNO₂)

Aniline (ArNH2)

Fe/HCl

Nitro —> amine

Sn/HCl

Nitro —> amine

LiAlH₄

Amide (has carbonyl)

Makes amine gets rid of carbonyl

H₂/Ni

Imine/Iminium

To amine

NaBH₃CN

Carbonyl + amine and turns it to just amine combines them and takes away carbonyl

RX (alkyl halide)

Adds alkyl groups to amines

1° → 2°

2° → 3°

3° → 4° ammonium salt

Heat + quaternary ammonium hydroxide

➡ Hofmann elimination

➡ Least substituted alkene

HNO₃

(on protected aniline)

Adds NO2 to aromatic ring

NaNO₂/HCl

Secondary amine

➡ Nitrosamine (N–N=O

NaNO₂/HCl

Primary aryl amine

Dizonium salt

H₂O, heat

ArN₂⁺ → ArOH

KI

ArN₂⁺ → ArI

HBF₄, heat

ArN₂⁺ → ArF

CuCl

ArN₂⁺ → ArCl

CuBr

ArN₂⁺ → ArBr

CuCN

ArN₂⁺ → ArCN

H₃PO₂

ArN₂⁺ → ArH

Activated aromatic ring + diazonium salt

Azo compound