Hydrogen Bromide → 6-Butylaminomethyl-naphthalen-2-ol

HRID 1357297Notes

Reaction equation

HRID 1357297 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17]C)[CH:13]=2)[CH:8]=1)[CH2:2][CH2:3][CH3:4].Br>C(O)(=O)C>[CH2:1]([NH:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([OH:17])[CH:11]=[CH:10]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 18505348Butyl-(6-methoxy-naphthalen-2-ylmethyl)-amine

Product 1

HCID 185053566-Butylaminomethyl-naphthalen-2-olYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of butyl-(6-methoxy-naphthalen-2-ylmethyl)-amine (10.0 g, 41.09 mmol), prepared in the previous step, 300 mL of 48% HBr and 200 mL of glacial acetic acid was refluxed under nitrogen for 19 h (overnight). The solvent was removed under reduced pressure. The resulting residue was partitioned between ethyl acetate and 5% sodium bicarbonate. The organic layer was separated, dried (MgSO4) and the solvent removed under reduced pressure to give 6-butylaminomethyl-naphthalen-2-ol (7.54 g, 80%) as a brown solid, mp 108-112° C.

Workup

  1. temperaturewas refluxed under nitrogen for 19 h (overnight)
  2. customThe solvent was removed under reduced pressure
  3. customThe resulting residue was partitioned between ethyl acetate and 5% sodium bicarbonate
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-749a4878ed2b451a93bd2f19655cb568
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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