Ethanol → 6-[[2-(2-Ethyl-3,4-dimethoxyphenyl)ethyl]amino]-6-oxohexanoic acid

HRID 1493752Notes

Reaction equation

HRID 1493752 reaction equation
[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[CH2:13][CH2:14][NH:15][C:16](=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]C)=[O:22])[CH3:2].[OH-].[Na+].C(O)C>O>[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[CH2:13][CH2:14][NH:15][C:16](=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 14346544Methyl 6-[[2-(2-ethyl-3,4-dimethoxyphenyl)ethyl]amino]-6-oxohexanoate

Product 1

HCID 143465456-[[2-(2-Ethyl-3,4-dimethoxyphenyl)ethyl]amino]-6-oxohexanoic acidYield 79.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the product from Stage (i) (11 g), 2N sodium hydroxide solution (200 ml) and ethanol (300 ml) was heated under reflux for 1 h. The solution was cooled and poured into water (1000 ml). The mixture was washed with ether, acidified with 2N hydrochloric acid and then extracted with ether. The extracts were washed with water, dried and evaporated to give the title compound (8.4 g) as a white solid, m.p. 92°-94°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. temperatureThe solution was cooled
  4. washThe mixture was washed with ether
  5. extractionextracted with ether
  6. washThe extracts were washed with water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-fd9a1390633549c088432a9f1a2df724
Source dataset
uspto-grants-1991_06
Patent number
US05023378

Reaction notes

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