2-(Methylamino)ethanol → 2-Aminobenzaldehyde

HRID 358856Notes

Reaction equation

HRID 358856 reaction equation
C[NH:2]CCO.F[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[NH2:2][C:13]1[CH:14]=[CH:7][CH:8]=[CH:9][C:10]=1[CH:11]=[O:12]

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 682552-Aminobenzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

Following the procedure described in U.S. Pat. No. 4,808,332, a reactor is charged with 2-(methylamino)ethanol (134 g, 1.8 moles), 4-fluorobenzaldehyde (74.4 g, 0.6 mole), potassium carbonate (82.8 g, 0.6 mole) and dimethylsulfoxide (750 ml), and the mixture is heated at 95° C. for 72 hours. The product mixture is cooled and poured into three liters of ice water. The yellow solid that precipitates is filtered, washed with water, and dried in a vacuum oven, mp 72° C. The 4-[N-(2-hydroxyethyl)-N-methylamino]benzaldehyde product is recrystallized from water as needle-like crystals.

Workup

  1. temperatureThe product mixture is cooled
  2. customThe yellow solid that precipitates
  3. filtrationis filtered
  4. washwashed with water
  5. customdried in a vacuum oven, mp 72° C
  6. customThe 4-[N-(2-hydroxyethyl)-N-methylamino]benzaldehyde product is recrystallized from water as needle-like crystals

Sources & evidence

ORD record
ord-d9bced5adf3b460d8ed723b18218013a
Source dataset
uspto-grants-1991_03
Patent number
US04997977

Reaction notes

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