Bromide ion → 6-Methylaminomethyl-naphthalen-2-ol

HRID 1357253Notes

Reaction equation

HRID 1357253 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][NH2+:13][CH3:14])[CH:6]=[CH:5]2.[Br-].C(=O)(O)[O-].[Na+]>O>[CH3:14][NH:13][CH2:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([OH:1])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 259Bromide ionHCID 516892Sodium BicarbonateHCID 18505274HCID 18505274, compound

Product 1

HCID 185052756-Methylaminomethyl-naphthalen-2-olYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(6-Hydroxy-naphthalene-2-ylmethyl)-methyl-ammonium; bromide (9 g, 33.56 mmol), prepared in step 3 of Example 31, was taken up in 300 mL of water and made basic by the addition of with 5% sodium bicarbonate. Some solid remained in the solution, which was removed by filtration. The filtrate was extracted with ethyl acetate multiple times. The organic extracts were combined, dried (MgSO4) and the solvent removed under reduced pressure to give 6-methylaminomethyl-naphthalene-2-ol (5 g, 80%) as a tan solid, mp 168-169° C.

Workup

  1. customwas removed by filtration
  2. extractionThe filtrate was extracted with ethyl acetate multiple times
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-349f56ef5ac449fcb59dfa63df235d46
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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