N-Methylaniline → HCID 19438627, compound

HRID 1733860Notes

Reaction equation

HRID 1733860 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)(O)[O-].[Na+]>>[CH3:1][N:2]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 7515N-MethylanilineHCID 117544Ethyl 6-bromohexanoateHCID 516892Sodium Bicarbonate

Product 1

HCID 19438627HCID 19438627, compoundYield 72.5%

Conditions

Temperature
120 °C

Procedure

A mixture of N-methylaniline (25 g) and ethyl 6-bromohexanoate (50 g) was stirred at 120° C. for 24 hours. After cooling, an aqueous sodium bicarbonate was added to make the mixture alkaline. Then the resulting mixture was extracted with ethyl acetate, washed with brine and dried over anhydrous sodium sulfate. The mixture was concentrated under reduced pressure and distilled to obtain ethyl 6-(N-methylanilino)hexanoate (40.5 g).

Workup

  1. temperatureAfter cooling
  2. extractionThen the resulting mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe mixture was concentrated under reduced pressure
  6. distillationdistilled

Sources & evidence

ORD record
ord-b3341247d9874c48a3b6262c23f10a74
Source dataset
uspto-grants-1996_07
Patent number
US05532171

Reaction notes

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