Quinine

C₂0H₂₄N₂O₂

Part 1 of 1

100 °C, 30 min, 94 %

H₂SO₄

H₂O
0 °C to RT, 48 h, 64 %

See the Pomeranz-Fritsch Isoquinoline Synthesis

Piperidine, CH₂O

EtOH, H₂O
100 °C, 6 h, 61 %

See the Betti Reaction

NaOMe

MeOH
220 °C, 16 h, 65 %

H₂, PtO₂
4 atm

AcOH
RT, 18 h

Ac₂O

MeOH
40-50 °C, 95 % (2 steps)

H₂, Ni (Raney)
200 atm

EtOH
150 °C, 16 h

CrO₃

AcOH, H₂O
0 to 50 °C, ON, 30% (2 steps)

See the Jones Oxidation

EtONO, NaOEt

EtOH
0 °C, 18 h, 78 %

H₂, PtO₂
3 atm

AcOH
RT, 40 h

MeI, K₂CO₃

EtOH
Reflux, 48 h, 91% (2 steps)

NaOH

H₂O
180 °C, 60 min, 38 %

See the Hofmann Elimination

HCl

EtOH
Reflux

See the Fischer Esterification

BzCl, K₂CO₃

CHCl₃, H₂O
Reflux, 2 h, 96 % (2 steps)

See the Schotten-Baumann Reaction

NaOEt

82 °C, 14 h, 63 %

See the Claisen Condensation

HCl

H₂O
Reflux, 4 h, 50 %

The enantiomers were resolved with (+)-tartaric acid and dibenzoyl-(+)-tartaric acid (11 % yield).

Remaining...

2.4 % (3 steps)

See : Chem. Ber. 1918, 51, 466; Angew. Chem. Int. Ed. 2008, 47, 1736.