Water → 3-[(Methylamino)methyl]benzenemethanol

HRID 2228726Notes

Reaction equation

HRID 2228726 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8](OC)=[O:9])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:1][NH:2][CH2:3][C:5]1[CH:6]=[C:7]([CH2:8][OH:9])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 12810606HCID 12810606, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 128106073-[(Methylamino)methyl]benzenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of methyl 3-[(methylamino)carbonyl]benzoate (preparation 11) (5.0 g, 20.7 mmol) in THF (120 ml) was treated dropwise with a solution of lithium aluminium hydride (1M, 30 ml, 30 mmol) in THF. The resultant slurry was stirred under reflux overnight, cooled and treated with water (1.1 ml), 15% NaOH (1.8 ml) and water (2.5 ml). The resultant gel was removed by filtration, the liquors concentrated in vacuo and taken up in ethyl acetate (120 ml). The organic layer was washed with sat aq brine (100 ml) and dried over MgSO4. Removal of the drying agent by filtration followed by evaporation of the solvent gave an oil which was purified by chromatography (SiO2, gradient elution with CH2Cl2; 95:5 CH2Cl2:MeOH; 90:10 CH2Cl2:MeOH; 90:10:1 CH2Cl2:MeOH:NH3; 85:15:1 CH2Cl2:MeOH:NH3). The second eluted material proved to be the correct product (2.9 g, 69%,). 1H NMR (CDCl3) δ 2.20 (s, 2H), 2.40 (s, 3H), 3.70 (s, 2H), 4.60 (s, 2H), 7.20-7.40 (m, 4H). LRMS m/z=152.4 (M+1)+.

Workup

  1. temperatureunder reflux overnight
  2. temperaturecooled
  3. customThe resultant gel was removed by filtration
  4. concentrationthe liquors concentrated in vacuo
  5. washThe organic layer was washed with sat aq brine (100 ml)
  6. dry with materialdried over MgSO4
  7. customRemoval of the drying agent
  8. filtrationby filtration
  9. customfollowed by evaporation of the solvent
  10. customgave an oil which
  11. customwas purified by chromatography (SiO2, gradient elution with CH2Cl2; 95:5 CH2Cl2:MeOH; 90:10 CH2Cl2:MeOH; 90:10:1 CH2Cl2:MeOH:NH3; 85:15:1 CH2Cl2:MeOH:NH3)

Sources & evidence

ORD record
ord-de097a630e794eebb4282d6289eff18b
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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