Hydrochloric Acid → N-nitroso-N-(5-methoxycarbonylpentyl)-aniline

HRID 1633151Notes

Reaction equation

HRID 1633151 reaction equation
[N:1]([O-:3])=O.[Na+].[CH3:5][O:6][C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:8].Cl>O>[N:1]([N:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:7]([O:6][CH3:5])=[O:8])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 20441676Methyl 6-(phenylamino)hexanoateHCID 23668193Sodium Nitrite

Product 1

HCID 13362122N-nitroso-N-(5-methoxycarbonylpentyl)-aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.4 g of sodium nitrite in 5 ml of water is added dropwise at 0°-10° to a mixture of 4.42 g of N-(5-methoxycarbonylpentyl)-aniline, 2.9 ml of concentrated hydrochloric acid, and ice as needed to maintain the desired temperature. The mixture is then allowed to stir at ambient temperature for 1 hour and is then extracted with ether. The extract is washed with water, dried over magnesium sulfate, and evaporated in vacuo to give N-nitroso-N-(5-methoxycarbonylpentyl)-aniline as an oil.

Workup

  1. temperatureto maintain the desired temperature
  2. extractionis then extracted with ether
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-13e73071e92d43899593294fa55b015d
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

Loading…