Acetonitrile → (2-Propoxy-3-methoxy-benzyl)methylamine

HRID 1711822Notes

Reaction equation

HRID 1711822 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.Br[CH2:13][CH2:14][CH3:15].C([O-])([O-])=O.[K+].[K+].C[C:23]#[N:24]>>[CH3:11][O:10][C:9]1[C:2]([O:1][CH2:13][CH2:14][CH3:15])=[C:3]([CH:6]=[CH:7][CH:8]=1)[CH2:4][CH2:23][NH2:24]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 78401-BromopropaneHCID 8991o-VanillinHCID 11430Potassium Carbonate

Product 1

HCID 20982692(2-Propoxy-3-methoxy-benzyl)methylamine

Procedure

A suspension of 2-hydroxy-3-methoxy-benzaldehyde (10.0 g, 65.6 mmol), 1-bromopropane (60 mL, 657 mmol) and K2CO3 (11.3 g, 82.1 mmol) in MeCN (250 mL) was heated to reflux for 12 h. The mixture was cooled to ambient temperature and the solution filtered. The filtrate was concentrated to give the title compound (12.9 g, quantitative) as light yellow oil: MS (ESI) m/e 195 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 h
  3. filtrationthe solution filtered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-68c23e62911d4a82aff90499d4834e42
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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