Benzaldehyde → HCID 9855876, compound

HRID 598225Notes

Reaction equation

HRID 598225 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>ClCCl.O.C(O)(=O)C>[CH3:9][O:8][C:5]1[N:6]=[CH:7][C:2]([NH:1][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 811216-Methoxy-3-pyridinylamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 9855876HCID 9855876, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-amino-2-methoxypyridine (1.00 g, 8.06 mmol) in dichloromethane (20.0 mL) was treated with benzaldehyde (0.080 mL, 8.06 mmol) followed by stirring at ambient temperature for 20 min. The mixture was then treated with sodium cyanoborohydride (1.79 g, 8.46 mmol) followed by acetic acid (0.460 mL, 8.06) and continued stirring for 2 h. The solution was treated with water and saturated sodium hydrogen carbonate, and then extracted twice with dichloromethane. The combined organic portions were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil was swirled in hexanes, and a solid was filtered. The filtrate was concentrated and the title compound was obtained as a light pink solid (0.340 g, 20%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.61 (d, J=2.5 Hz, 1H), 7.28-7.41 (m, 5H), 7.01 (dd, J=8.8, 3.0 Hz, 1H), 6.62 (d, J=9.3 Hz, 1H), 4.30 (s, 2H), 3.87 (s, 3H). MS(ES+) m/e 215 [M+H]+.

Workup

  1. stirringcontinued stirring for 2 h
  2. extractionextracted twice with dichloromethane
  3. dry with materialThe combined organic portions were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationa solid was filtered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-42aec102a8b84b10aec13ccdad0d4ea9
Source dataset
uspto-grants-2011_03
Patent number
US07897612B2

Reaction notes

Loading…