Sodium borohydride → HCID 12378777, compound

HRID 505353Notes

Reaction equation

HRID 505353 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:6]=[N:7][CH2:8][CH:9]([O:12][CH3:13])[O:10][CH3:11].[BH4-].[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:6][NH:7][CH2:8][CH:9]([O:10][CH3:11])[O:12][CH3:13]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 1125379939964-87-9

Product 1

HCID 12378777HCID 12378777, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Imine 11a (13.90 g, 0.055 mol) was dissolved in ethanol (50 mL) and NaBH4 (4.2 g) was added over 1 h while stirring the reaction mixture at reflux. The reaction was diluted with water (250 mL). The amine was extracted into chloroform (300 mL) washed with water (2×200 mL), brine (200 mL), dried Na2SO4 and concentrated to provide a yellow liquid (12.88 g, 91.7%). 1H NMR (300 MHz CDCl3) 6.81 (s, 1H), 6.78 (d, J=8.1 Hz, 1H), 6.74 (d, J=8.1, 1H), 4.41 (t, J=5.4 Hz, 1H), 3.81 (s, 3H), 3.79 (s, 3H), 3.67 (s, 2H), 3.29 (s, 6H), 2.67 (d, J=5.4 Hz, 2H).

Workup

  1. temperatureat reflux
  2. extractionThe amine was extracted into chloroform (300 mL)
  3. washwashed with water (2×200 mL), brine (200 mL), dried Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fc465021a8794066bea881eaa5338644
Source dataset
uspto-grants-2010_08
Patent number
US07781445B2

Reaction notes

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