Looks like somebody needed an excuse to waste a lot of 2C-B
J. Med. Chem. 27(4), 513-520 (1984)
(
https://www.thevespiary.org/rhodium/Rhodium/pdf/2c-c.2c-cn.synthesis.pdf)
2,5-dimethoxy-4-bromophenyl-2-(phthalimidoamino)-ethane (11d)
To a solution of 11c (2CB freebase) (7.24 g, 27.8 mmol) and phthalic
anhydride (4.5 g, 30 mmol) in 100 mL of DMF (disilled) was added molecular
sieves. The reaction mixture was heated under reflux overnight and, after
cooling, was suction filtered to remove the molecular sieves. Treatement
with CH2Cl2 resulted in the formation of yellow needles. Recrystallization
from EtOH provided 7.57 g (69%) of 11d: mp 141.5-142'C.
2,5-dimethoxy-4-cyanophenyl-2-(phthalimidoamino)-ethane (12d)
Compound 11d (7.57 g, 19.4 mmol) and cuprous cyanide (2.0 g , 22.3 mmol) in
150 mL of DMF were heated under reflux for 5 h. The mixture was poured into
a solution containing hydrated ferric chloride (6g), 1.48 mL of concentrated
HCl, and 9 mL of water. The solution was maintained at a temperature of
60-70'C for 20 min. to decompose the complex and then extracted with
CH2CL2. The orgranic phase was washed with diluted aqeuous HCl (100mL),
dried (MgSO4) and evaporated to give a white solid. Recrystallization from
EtOH provided 5.96 g (91%) of 12d as white needles. mp 194-195'C.
1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane (12c)
Phthalimide 12d (9.2 g, 27.38 mmol) and hydrazine (2.2 mL, 68.55 mmol, 98%)
in 50 mL of anhydrous EtOH were heated under reflux for 15 min. After the
mixture was cooled, the phthalazinedione was filtered off, and the filtrate
was evaporated to give a solid residue. The solid was dissolved in H2O and
extracted with CHCl3. The organic extract was washed with aqeous Na2CO3
(10%, 3x100mL), dried (Na2SO4) and evoparated to give 3.6 g (64%) of 12c.
The HCl salt (precipitated from ether) was recrystallized from EtOH, mp
220-222'C.