Acetic Acid → HCID 43719715, compound

HRID 413318Notes

Reaction equation

HRID 413318 reaction equation
[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH:12](=O)[CH2:13][CH3:14].CC(O)=O.[BH3-]C#N.[Na+]>CO>[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 117832-Methyl-3-nitroanilineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 43719715HCID 43719715, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-3-nitroaniline (0.5 g, 3.3 mmol) and MeOH (20 mL) was added propionaldehyde (2.3 mL, 33 mmol), AcOH (1.9 mL, 33 mmol), and NaBH3CN (2 g, 33 mmol). Reaction was stirred at rt for 2 hours then quenched with H2O and concentrated in vacuo. Diluted with EtOAc (20 mL) and adjusted to pH=7 with saturated NaHCO3. Washed organic layer with H2O (3×10 mL) and brine (3×10 mL), dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash chromatography (5% EtOAc/hex) to afford 0.7 g of the 2-methyl-3-nitro-N-propylaminobenzene. A solution of the product and EtOAc (25 mL) was hydrogenated over 10% Pd/C (70 mg) at rt and 1 atm. After 15 hours filtered reaction mixture through a pad of Celite and concentrated the filtrate to afford the desired Compound 568 (0.10 g) as yellow oil.

Workup

  1. customReaction
  2. customthen quenched with H2O
  3. concentrationconcentrated in vacuo
  4. additionDiluted with EtOAc (20 mL)
  5. dry with materialWashed organic layer with H2O (3×10 mL) and brine (3×10 mL), dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (5% EtOAc/hex)

Sources & evidence

ORD record
ord-456575228f22405d88da04d4cc43a052
Source dataset
uspto-grants-2003_05
Patent number
US06566372B1

Reaction notes

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