Sodium Hydroxide → 2-[3-Methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethylamine

HRID 650980Notes

Reaction equation

HRID 650980 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:26]=[C:25]([CH:27]=[CH:28][N+:29]([O-])=O)[CH:24]=[CH:23][C:10]=1[O:11][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>O1CCCC1>[CH3:7][O:8][C:9]1[CH:26]=[C:25]([CH2:27][CH2:28][NH2:29])[CH:24]=[CH:23][C:10]=1[O:11][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 538700371-[2-Methoxy-4-(2-nitro-vinyl)-phenoxymethyl]-naphthalene

Product 1

HCID 217101572-[3-Methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10 g of lithium aluminium hydride are placed in 200 ml of tetrahydrofuran; the mixture is stirred at room temperature. 25.8 g of 1-[2-methoxy-4-(2-nitro-vinyl)-phenoxymethyl]-naphthalene dissolved in 300 ml of tetrahydrofuran are added dropwise thereto over a period of 90 minutes. The reaction mixture is heated at reflux for 4 hours. After cooling, 40 ml of 1 N sodium hydroxide solution are cautiously added dropwise, external cooling being effected using an ice bath. When the addition is complete, the reaction mixture is stirred, without cooling, for one hour, then filtered with suction over Celite and washed with a small amount of tetrahydrofuran. The filtrate is dried over potassium carbonate and concentrated by evaporation, yielding 2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethylamine in the form of a brown oil.

Workup

  1. additionare added dropwise
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 4 hours
  4. temperatureAfter cooling
  5. temperatureexternal cooling
  6. additionWhen the addition
  7. stirringthe reaction mixture is stirred
  8. temperaturewithout cooling, for one hour
  9. filtrationfiltered with suction over Celite
  10. washwashed with a small amount of tetrahydrofuran
  11. dry with materialThe filtrate is dried over potassium carbonate
  12. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-394898bf230a4a36b0d35ae24f7e562b
Source dataset
uspto-grants-2001_08
Patent number
US06277849B1

Reaction notes

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