Aniline → Methyl 6-(phenylamino)hexanoate

HRID 1633150Notes

Reaction equation

HRID 1633150 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15].O.O.O.C([O-])(=O)C.[Na+]>C(O)C>[CH3:17][O:16][C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:15]

Participants

5

Reactant 3

HCID 6115AnilineHCID 4170292Methyl 6-BromohexanoateHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 20441676Methyl 6-(phenylamino)hexanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aniline (2.79 g, 2.73 ml), 6.27 g of methyl 6-bromohexanoate and 12.24 g (0.09 mole) of sodium acetate trihydrate are heated at 80°-100° overnight in 15 ml of absolute ethanol. After cooling, the mixture is poured into 75 ml of ice-water and extracted with ether. The organic extract is washed with water, dried over magnesium sulfate and evaporated in vacuo to give N-(5-methoxycarbonylpentyl)aniline.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether
  3. extractionThe organic extract
  4. washis washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-3ac78de5eb604d259375d050c0e78e7f
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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