Acetic Acid → HCID 33788030, compound

HRID 885454Notes

Reaction equation

HRID 885454 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, compound

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 overnight. The resulting mixture was then 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 MS 163 (M+1)+

Workup

  1. customThe ice bath was removed
  2. additionThe resulting mixture was then 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-e789de48dd5249f6a95c155f56302e31
Source dataset
uspto-grants-2012_08
Patent number
US08242157B2

Reaction notes

Loading…