Isopropylamine → Methyl 3-[2-(2-hydroxy-3-isopropylaminopropoxy)benzoyl]propionate

HRID 596673Notes

Reaction equation

HRID 596673 reaction equation
[O:1]1[CH2:19][CH:2]1[CH2:3][O:4][C:5]1[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=1[C:7]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:8].[CH:20]([NH2:23])([CH3:22])[CH3:21]>CO>[OH:1][CH:2]([CH2:19][NH:23][CH:20]([CH3:22])[CH3:21])[CH2:3][O:4][C:5]1[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=1[C:7]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:8]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 13530373Methyl 3-[2-(2,3-epoxypropoxy)benzoyl]propionate

Product 1

HCID 20309568Methyl 3-[2-(2-hydroxy-3-isopropylaminopropoxy)benzoyl]propionateYield 101.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred mixture of methyl 3-[2-(2,3-epoxypropoxy) benzoyl]-propionate (8.3g, 0.031 mole), methanol (85 ml), and isopropylamine (16.4 ml, 0.19 mole) was heated under reflux for 90 minutes. Evaporation of the solution under reduced pressure gave methyl 3-[2-(2-hydroxy-3-isopropylaminopropoxy)benzoyl]propionate (10.2 g, 100%)as a pale brown oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 90 minutes
  3. customEvaporation of the solution under reduced pressure

Sources & evidence

ORD record
ord-8a471cf92ea44e6fa7be42d72d371012
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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