Benzoyl chloride → HCID 67272541, compound

HRID 1592421Notes

Reaction equation

HRID 1592421 reaction equation
[NH2:1][C:2]1[C:3]([CH2:8][OH:9])=[N:4][CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[OH:9][CH2:8][C:3]1[C:2]([NH:1][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 15645802(3-Aminopyridin-2-yl)methanol

Product 1

HCID 67272541HCID 67272541, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3-amino-pyridin-2-yl)-methanol (0.310 g, 2.54 mmol) and Et3N (0.570 g, 5.33 mmol) in dry CH2Cl2 (20 mL) was added benzoyl chloride (0.700 g, 5.08 mmol) dropwise. After the mixture was stirred for 18 h CH2Cl2 was removed, and then MeOH (5 mL) and saturated aqueous K2CO3 (25 mL) were added. The mixture was stirred for 2 h, and then extracted with CH2Cl2 (5×50 mL). The combined extracts were dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (2:1 CH2Cl2/Et2O), affording N-(2-hydroxymethyl-pyridin-3-yl)-benzamide as a white solid. The white solid was dissolved in CH2Cl2 (15 mL), and activated MnO2 (0.660 g, 7.68 mmol) was added. The suspension was stirred for 64 h, and then filtered through a celite cake. The filtrate was concentrated by evaporation under vacuum, and a brown residue was purified by flash chromatography on a silica gel column (4:1 CH2Cl2/Et2O), affording N-(2-formyl-pyridin-3-yl)-benzamide as a pale yellow solid (0.139 g, 24% two steps). 1H NMR (CDCl3) δ 7.54-7.62 (m, 4H), 8.07 (d, 2H, J=7.2 Hz), 8.54 (d, 1H, J=4.2 Hz), 9.32 (d, 1H, J=8.7 Hz), 10.19 (s, 1H).

Workup

  1. customwas removed
  2. additionMeOH (5 mL) and saturated aqueous K2CO3 (25 mL) were added
  3. extractionextracted with CH2Cl2 (5×50 mL)
  4. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed by evaporation under vacuum
  7. customthe residue was purified by flash chromatography on a silica gel column (2:1 CH2Cl2/Et2O)

Sources & evidence

ORD record
ord-6e185d3207cf44d3a4f0455796312416
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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