Triethylamine → HCID 178436623, compound

HRID 2065910Notes

Reaction equation

HRID 2065910 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[C:5]([CH2:15][CH3:16])[CH:4]=1)#[N:2].CCN(CC)CC.Cl.[NH2:25][OH:26]>CCO>[CH2:15]([C:5]1[CH:4]=[C:3]([C:1](=[NH:2])[NH:25][OH:26])[CH:8]=[C:7]([CH3:9])[C:6]=1[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 574374143-(4-Cyano-2-ethyl-6-methylphenyl)propionic acid

Product 1

HCID 178436623HCID 178436623, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(4-cyano-2-ethyl-6-methyl-phenyl)-propionic acid (10.0 g, 46.0 mmol) in EtOH (80 mL), NEt3 (13.97 g, 138.1 mmol) followed by hydroxylamine hydrochloride (6.40 g, 92.1 mmol) is added. The mixture is refluxed for 7 h before it is cooled to rt. The solvent is removed in vacuo. The residue is dissolved in 2 N aq. HCl and the pH is adjusted to 5 by adding 32% aq. NaOH solution. The precipitate that forms is collected, washed with water and dried under high vacuum at 40° C. for 18 h to give 3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenyl]-propionic acid (11.7 g) as a beige crystalline powder; LC-MS: tR=0.60 min, [M+1]+=251.09.

Workup

  1. additionis added
  2. temperatureThe mixture is refluxed for 7 h before it
  3. customThe solvent is removed in vacuo
  4. dissolutionThe residue is dissolved in 2 N aq. HCl
  5. additionby adding 32% aq. NaOH solution
  6. customThe precipitate that forms is collected
  7. washwashed with water
  8. customdried under high vacuum at 40° C. for 18 h

Sources & evidence

ORD record
ord-e3a5cf88dcae4e0d86562675fc92a00d
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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