Hydrochloric Acid → (5-Bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amine

HRID 1357270Notes

Reaction equation

HRID 1357270 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH:16]=[N:17][CH3:18])=[CH:9]2.Cl>C(O)C>[Br:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH2:16][NH:17][CH3:18])=[CH:9]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 18505272(5-Bromo-6-methoxy-naphthalen-2-ylmethylene)-methyl-amine

Product 1

HCID 18505315(5-Bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amineYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (131 mg, 3.47 mmol) was added under nitrogen to a warm solution of (5-bromo-6-methoxy-naphthalen-2-ylmethylene)-methyl-amine (950 mg, 4.41 mmol), prepared in the previous step, in 30 mL of absolute ethanol. After the addition the reaction was stirred at room temperature for 19 h (overnight). 1 N HCl was added dropwise until the reaction was pH˜1 (litmus paper). The solvent was removed under reduced pressure and the residue partitioned between methylene chloride and water. The aqueous layer was made basic by the addition of 1 N NaOH. The organic layer was separated and the aqueous layer was extracted three times with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure to give (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amine (900 mg, 94%) as an off-white solid, mp 41-45° C.

Workup

  1. additionAfter the addition the reaction
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between methylene chloride and water
  4. additionThe aqueous layer was made basic by the addition of 1 N NaOH
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted three times with methylene chloride
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-bbceb141f3374b4e85e5c9b7cfdfe4eb
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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