Acetic Acid → HCID 33788030, compound

HRID 2098359Notes

Reaction equation

HRID 2098359 reaction equation
[C:1]1([NH2:8])[C:2]([NH2:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH:9]1([CH:12]=O)[CH2:11][CH2:10]1.[BH3-]C#N.[Na+].C(O)(=O)C>CO>[CH:9]1([CH2:12][NH:7][C:2]2[C:1]([NH2:8])=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7243O-PhenylenediamineHCID 123114CyclopropanecarboxaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 33788030HCID 33788030, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzene-1,2-diamine (1.62 g, 15.0 mmol) and cyclopropanecarbaldehyde (1.05 g, 15.0 mmol) in MeOH (15 mL) at 0° C. was added NaCNBH3 (2.07 g, 33.0 mmol) and acetic acid (0.2 mL). The ice bath was removed and the resulting mixture was stirred at room temperature over night. The resulting mixture was diluted with EtOAc, washed with H2O, dried over Na2SO4, filtered, and concentrated in vacuo. The resultant residue was purified by flash column chromatography (SiO2), eluting with a hexanes-EtOAc gradient to yield N-cyclopropylmethyl-benzene-1,2-diamine (836 mg, 34%). MS 163 (M+1)+.

Workup

  1. customThe ice bath was removed
  2. additionThe resulting mixture was diluted with EtOAc
  3. washwashed with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by flash column chromatography (SiO2)
  8. washeluting with a hexanes-EtOAc gradient

Sources & evidence

ORD record
ord-09e18029e15c45df8106cd59c1c7834a
Source dataset
uspto-grants-2013_05
Patent number
US08450497B2

Reaction notes

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