Sulfuric Acid → HCID 67107381, compound

HRID 1910755Notes

Reaction equation

HRID 1910755 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:11][C:12]1[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]([CH:19]=O)[CH:13]=1.S(=O)(=O)(O)O.C([BH3-])#N.[Na+]>O1CCCC1.O>[CH3:11][C:12]1[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]([CH2:19][NH:8][C:7]2[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:13]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 74754-NitroanilineHCID 2255194,6-Dimethylpyridine-2-carbaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 67107381HCID 67107381, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

p-Nitroaniline (0.51 g, 3.7 mmol) was added to a solution of 4,6-dimethyl-pyridine-2-carbaldehyde (0.5 g, 3.7 mmol) in tetrahydrofuran (20 mL) at 0° C., followed by sulfuric acid and water (1 mL:1 mL). After stirring at 0° C. for 30 min. sodium cyanoborohydride (0.47 g, 7.4 mmol) was added portionwise at 0° C. The mixture stirred at room temperature for 1 h then concentrated in vacuo, diluted with water and extracted with ethyl acetate. The organic phase was washed with sodium carbonate solution, dried over anhydrous sodium sulfate and concentrated to give a residue which was purified by column chromatography on silica gel (60-120 mesh) using 18% ethyl acetate/hexane as eluent to afford (4,6-dimethyl-pyridin-2-ylmethyl)-(4-nitro-phenyl)-amine (0.35 g, 37%).

Workup

  1. additionwas added portionwise at 0° C
  2. concentrationthen concentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with sodium carbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto give a residue which
  9. customwas purified by column chromatography on silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-546a4594b4764603b54f16a17da1a817
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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