N,N,N',N'-Tetramethylmethanediamine → 1-[(dimethylamino)methyl]-2-naphthol

HRID 1598313Notes

Reaction equation

HRID 1598313 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[CH3:12][N:13]([CH2:15]N(C)C)[CH3:14]>O1CCOCC1>[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH2:12][N:13]([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 86632-Naphthol

Product 1

HCID 2231801-[(dimethylamino)methyl]-2-naphthol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-hydroxynaphthalene (20.18 g), N,N,N',N'-tetramethyldiaminomethane (19.10 ml) and 1,4-dioxane (200 ml) was heated on a steam bath for 24 hours and then evaporated to dryness under reduced pressure. The residue was dissolved in 2M hydrochloric acid and washed with ethyl acetate, neutralised with concentrated sodium hydroxide solution and extracted with dichloromethane to give a solid which was recrystallised from petroleum ether, b.p. 60°-80° C. to give 2-hydroxy-1-(dimethylaminomethyl)naphthalene, m.p. 79°-80° C.

Workup

  1. temperaturewas heated on a steam bath for 24 hours
  2. customevaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in 2M hydrochloric acid
  4. washwashed with ethyl acetate, neutralised with concentrated sodium hydroxide solution
  5. extractionextracted with dichloromethane
  6. customto give a solid which
  7. customwas recrystallised from petroleum ether, b.p. 60°-80° C.

Sources & evidence

ORD record
ord-fb514cb2a4e5482caf62e5ddb5ea494a
Source dataset
uspto-grants-1998_04
Patent number
US05736568

Reaction notes

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