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			Some Fluoro and nitro analogs of TMA-2 and MMDA-2 
                      Synthetic Communications 24(3), 417-426)
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OK, actually this is a supplement to PIHKAL, since its covers the synths for 
fluoro- and nitroanalogs of 2,4,5-MeO-amphetamine TMA 2(#158, 20-40 mg, 8-12 h) 
and 2-methoxy-4,5-methylenedioxyamphetamine MMDA-2(#133, 25-50 mg, 8-12 h). 

1-(2-NO2-4,5-diMeOphenyl)-2-aminopropane:

A solution of 1-(3,4-diMeOphenyl)-2-aminopropane (1.95 g, 10 mmol) in 2N HNO3 
(10 ml) was added with stirring at 15°C to a concentrated solution of nitric 
acid (d 1.4, 30 ml) diluted with water (12 ml). Stir for 3 hrs at STP, then 
pour into ice-water. Precipitate was suspended in 0.1 M NaOH solution, free 
amine was extracted with CH2Cl2, solvent was dried and evaporated. Redissolve 
in PhMe and bubble HCL through it to get 1.9 g (69 % yield) of the title cpd. 

1-(2-NO2-4,5-benzodioxole)isopropylamine:

Prepared in a similar way as described above, by nitration of MDA in 80% yield. 

2,4-dimethoxy-5-fluorobenzaldehyde:

Phosphorus oxychloride (15.3 g, 0.1 mol) and N-methyl formanilide (13.5 g, 
0.1 mol) was stirred for 30 mins at 25°C. Add slowly 2,4-dimethoxyfluorobenzene 
(15.6 g, 0.1 mol). After addition is complete, let react for 3 hrs at 35°C, 
leave overnight and pour in ice-water. Filter precipitate and dry to give 
17.7 g fluorobenzaldehyde (96% yield) 

1-(2-F-4,5-diMeO)-2-nitropropene: 

A mixture of 2-fluoro-4,5-benzaldehyde (4 g, 0.02 mol) and ammonium acetate 
(0.38 g, 5 mmol) in nitroethane (21 ml) was heated for 3 hrs at 80°C. Excess 
solvent was evaporated and the oily residue scratched with cold EtOH to 
precipitate the nitropropene (3.6 g, 69% yield) 

1-(2-F-4,5-diMeOphenyl)-2-aminopropane : 

To a suspension of LAH (0.8 g, 0.02 mol) in dry THF (10 ml) was added with 
stirring a solution of the above nitropropene (1 g, 4.1 mmol) in dry THF 
(15 ml). The resulting mixture was refluxed for 3 hrs. It was then cooled and 
excees LAH was decomposed by adding water. After filtration and washing the 
inorganic precipitate with Et2O, combined extracts were evaporated and the oily 
residue redissolved in 0.1 N H2SO4. Wash with ethre, basify and extract with 
CH2Cl2. Evaporate solvent and convert free base to hydrochloride salt by 
bubbling HCL through an ethereal solution of the base to get 0.6 g (58% yield) 
of the isopropylamine. 


The procedures can be found in: 
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1) Synth. Comm. 24, 417-26('94) 
2) PIHKAL by Dr. Shulgin

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