4-Methylbenzaldehyde → HCID 82019740, compound

HRID 1479896Notes

Reaction equation

HRID 1479896 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][NH2:19].C[Si]([C:24]#[N:25])(C)C>C(#N)C>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][NH:19][CH:6]([C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][CH:4]=1)[C:24]#[N:25]

Participants

5

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 812922-MethoxybenzylamineHCID 82115Trimethylsilyl cyanide

Product 1

HCID 82019740HCID 82019740, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-methylbenzaldehyde (4.38 g, 36 mmol) in 130 mL of acetonitrile at room temperature, 1-(2-methoxyphenyl)methanamine (5 g, 36 mmol) and trimethylsilyl cyanide (5.2 mL, 50 mmol) were added. The mixture was stirred for 16 h at room temperature until the starting materials had been completely consumed as judged by TLC (petroleum ether/ethyl acetate 90:10) and GC analysis. The mixture was quenched with 40 mL of saturated ammonium chloride, stirred for 15 min, added with 100 mL of water and then extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate 90:10) to afford [(2-methoxybenzyl)amino](4-methylphenyl)acetonitrile as a red oil (6.1 g, y=64%). 1H NMR (CDCl3) δ (ppm): 7.45 (d, 2H, J=7.3 Hz), 7.33-7.25 (m, 2H), 7.21 (d, 2H, J=7.2 Hz), 6.91-6.85 (m, 2H), 4.79 (s, 1H), 4.03 (d, 1H, J=13.2 Hz), 3.95 (d, 1H, J=13.2 Hz), 3.86 (s, 3H), 2.38 (s, 3H). MS (ES1+) m/z: 266.85 (M+1), 240.04 (M-HCN+1).

Workup

  1. customhad been completely consumed
  2. customThe mixture was quenched with 40 mL of saturated ammonium chloride
  3. stirringstirred for 15 min
  4. additionadded with 100 mL of water
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate 90:10)

Sources & evidence

ORD record
ord-10f248a0b78e4ff8880325196387ade2
Source dataset
uspto-grants-2016_08
Patent number
US09409876B2

Reaction notes

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