Acetic Acid → 6-(Benzylamino-methyl)-naphthalen-2-ol

HRID 1357294Notes

Reaction equation

HRID 1357294 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:20]C)[CH:16]=2)[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.C(O)(=O)C>O>[CH2:1]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 18505307Benzyl-(6-methoxy-naphthalen-2-ylmethyl)-amine

Product 1

HCID 185052776-(Benzylamino-methyl)-naphthalen-2-olYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of benzyl-(6-methoxy-naphthalen-2-ylmethyl)-amine (1.3 g, 4.7 mmol), prepared in the previous step, 65 mL of 48% HBr and 50 mL of glacial acetic acid was refluxed under nitrogen for 19 h (overnight). The solvent was removed under reduced pressure to give a red solid. The solid was suspended in 250 mL of water and heated until most of the solid dissolved. The mixture was filtered, the filtrate made basic with sodium bicarbonate and extracted three times with ethyl acetate. The organic extracts were combined, dried (MgSO4) and the solvent removed under reduced pressure to give 6-(benzylamino-methyl)-naphthalen-2-ol (0.76 g, 62%) as a green solid, mp 120-122° C.

Workup

  1. temperaturewas refluxed under nitrogen for 19 h (overnight)
  2. customThe solvent was removed under reduced pressure
  3. customto give a red solid
  4. temperatureheated until most of the solid
  5. dissolutiondissolved
  6. filtrationThe mixture was filtered
  7. extractionextracted three times with ethyl acetate
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ef2b79ca95fd4479b865ed56960bdc1c
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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