Triethylamine → Triethylamine methanol

HRID 1839847Notes

Reaction equation

HRID 1839847 reaction equation
[OH:1][C:2]1C2C(=CC=CC=2)OC(=O)C=1.Cl.ON.[CH2:16]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH3:17]>CO>[CH3:17][CH2:16][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20].[CH3:2][OH:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 546829304-Hydroxycoumarin

Product 1

HCID 22728368Triethylamine methanolYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Hydroxy-coumarin (10 grams), hydroxyl-amine hydrochloride (15 grams) and triethyl-amine (22 grams) in MeOH (50 mL) were heated at reflux for about 1.5 hours. The residue obtained after evaporation to dryness was dissolved in aqueous NaHCO3 and extracted with ether. After acidification of the aqueous phase the product was isolated by filtration and washed with water. The yield is about 73% (w/w).

Workup

  1. temperatureat reflux for about 1.5 hours
  2. customThe residue obtained
  3. customafter evaporation to dryness
  4. dissolutionwas dissolved in aqueous NaHCO3
  5. extractionextracted with ether
  6. customAfter acidification of the aqueous phase the product was isolated by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-4169b37b35564a0b97ecee815f4f63d7
Source dataset
uspto-grants-2004_01
Patent number
US06677458B2

Reaction notes

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