5-METHYL-2-NITROBENZALDEHYDE

5.5 ml (63.2 mmol) of oxalyl chloride were added to 50 ml of dichloromethane and cooled to -60° C. After 20 minutes, 9.13 ml (138.6 mmol) of DMSO were added and stirred at -60° C. followed 15 minutes later by the addition of 3.91 g (23.3 mmol) of the 3-hydroxymethyl-p-nitrotoluene obtained in Step 1 at -60° C. and stirring. After 30 minutes, 45 ml of triethylamine were dropped in at -60° C. and then returned to room temperature. After concentrating under reduced pressure, 0.1 M hydrochloric acid was added to the residue followed by extraction with ethyl acetate (150 ml.x.2). The organic phase was then dried with magnesium sulfate and concentrated under reduced pressure to obtain 5.02 g of the target compound (crude yield: 130percent).1 PREPARATION 6; 5-Methyl-lH-indole-7-carboxaldehyde a) 5-Methyl-2-nitrobenzaldehyde Dissolve (5-methyl-2-nitrophenyl) methanol (10 g, 59. 88 mmol) in dichloromethane (210 mL). Add 3A molecular sieves (54 g) and pyridinium dichromate (22.53 g, 59. 88 mmol). Stir at room temperature for 6 hours. Pass the crude reaction mixture through a short silica gel column, and remove under reduced pressure. Purification of the residue by flash chromatography (silica gel, 10-20percent ethyl acetate: hexane) gives 7.84 g (79percent) of title compound as colorless oil. 1H NMR (CDC13) 8 10. 41 (m, 1H), 8.02 (m, 1H), 7.69 (s, 1H), 7.53 (d, 1H), 2.51 (s, 3H).Step 2

Molecular Weight:165.15
XLogP3:1.6
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:165.042593085
Monoisotopic Mass:165.042593085
Topological Polar Surface Area:62.9
Heavy Atom Count:12
Complexity:187
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes