3-Amino-4-methoxybenzaldehyde

3-Amino-4-methoxybenzaldehyde was obtained by reduction of the corresponding nitro compound according to Tetrahedron Letters, 1993, 34(46), 7445-1446.General procedure: A solution of intermediate 3 (1 mmol) and commercially available aromatic aldehydes 4 (1 mmol) in CH3OH (10 mL) was stirred in ice bath for 30 min. Then slowly add 3 mL of 50% KOH aqueous solution. The mixture was stirred for 48 h at room temperature and poured into ice-cold water. After adjusted pH to 7 using HCl solution, the precipitate was collected on a paper filter and recrystallized from ethanol to obtain the title compounds (5a-5p).General procedure: To a solution of 10a-d (0.2 mmol) in anhydrous THF, NaH (60%, 0.24 mmol) was added at 0 C under N2 atmosphere. After stirringfor 15 min, acetyl protected isovanillin (0.24 mmol) was added intothe mixture and the reaction was stirred for another 1 h. The reactionmixture was then extracted with EtOAc (3 20 mL). Thecombined organic layers were then washed with saturated brine, dried over anhydrous Na2SO4, and concentrated in vacuo. Theresiduewas dissolved in MeOH (5 mL), 5% sodium hydroxide (5 mL)was added. After stirring for 30 min at room temperature, the reactionmixture was acidified by the addition of 10% aqueous HCl, and then diluted with EtOAc, washed with water, and brine successively, dried over anhydrous Na2SO4, and concentrated in vacuo.The residue was purified by flash column chromatography usingPE/EA (4/1, V/V) as an eluent to afford the compounds 12l, 12n-q, 13a-d.The product of a in Example 20 (100 mg, 0.27 mmol) was dissolved in dry THF.60% sodium hydrogen (18 mg, 0.4 mmol) was added under nitrogen.After stirring at 0 C for 15 minutes, The product of b in (50 mg, 0.13 mmol) was dissolved in dry THF.60% sodium hydrogen (7.8 mg, 0.20 mmol) was added under nitrogen.After stirring at 0 C for 15 minutes, The product of d (50 mg, 0.13 mmol) from was dissolved in dry tetrahydrofuran.60% sodium hydrogen (7.8 mg, 0.20 mmol) was added under nitrogen.After stirring at 0 C for 15 minutes, General procedure: To a solution of 10a (0.2 mmol) in anhydrous THF, NaH (60%, 0.24 mmol) was added at 0 C under N2 atmosphere. After stirringfor 15 min, aromatic aldehyde (0.24 mmol) was added into themixture and the reaction was stirred for another 1 h. The reactionmixture was then extracted with EtOAc (3 20 mL). The combinedorganic layers were then washed with saturated brine, dried overanhydrous Na2SO4, and concentrated in vacuo. The residue waspurified by flash column chromatography using PE/EA (5/1, V/V) asan eluent to afford the compounds 12a-k, 12m.

Molecular Weight:151.16
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:151.063328530
Monoisotopic Mass:151.063328530
Topological Polar Surface Area:52.3
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes