Sodium Hydroxide → HCID 57486961, compound

HRID 1021188Notes

Reaction equation

HRID 1021188 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:14]([CH:15]=[CH:16][N+:17]([O-])=O)=[C:13]([CH3:20])[C:12]([O:21][CH3:22])=[C:11]([CH3:23])[C:10]=1[CH3:24].[OH-].[Na+]>C1COCC1>[CH3:7][O:8][C:9]1[C:10]([CH3:24])=[C:11]([CH3:23])[C:12]([O:21][CH3:22])=[C:13]([CH3:20])[C:14]=1[CH2:15][CH2:16][NH2:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86653766HCID 86653766, compound

Product 1

HCID 57486961HCID 57486961, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirring suspension of lithium aluminum hydride (1.63 g, 42.8 mmol, 6.0 equiv) in THF (15 mL) at 0° C. was added a solution of 1,4-dimethoxy-2,3,5-trimethyl-6-(2-nitrovinyl)benzene (1.8 g, 7.14 mmol) in THF (15 mL) over 30 min. Following addition, the mixture was warmed to 60° C. and stirred for 2 hr. After this time, the reaction was deemed complete by HPLC analysis, the mixture was slowly transferred to 100 mL 6M aqueous sodium hydroxide and stirred for 20 min. The resulting suspension was filtered in vacuo and the cake rinsed with i-propyl acetate (200 mL). The organics were removed and the remaining aqueous layer was extracted 2× with i-propyl acetate (200 mL), combined, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 1.6 g of light brown oil, which solidified on standing to give crude amine 2-(2,5-dimethoxy-3,4,6-trimethylphenyl)ethanamine.1H NMR (CDCl3, 400 MHz) 3.63 (s, 3H), 3.59 (s, 3H), 2.79 (m, 2H), 2.63 (m, 2H), 2.20 (s, 3H), 2.15 (s, 3H) ppm.

Workup

  1. additionaddition
  2. stirringstirred for 20 min
  3. filtrationThe resulting suspension was filtered in vacuo
  4. washthe cake rinsed with i-propyl acetate (200 mL)
  5. customThe organics were removed
  6. extractionthe remaining aqueous layer was extracted 2× with i-propyl acetate (200 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b71cb65975240418c23ac4171643959
Source dataset
uspto-grants-2014_05
Patent number
US08716527B2

Reaction notes

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