(Aminooxy)acetic acid → HCID 54363749, compound

HRID 1386418Notes

Reaction equation

HRID 1386418 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=O)[CH2:14][CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:20]([CH2:23][O:24][NH2:25])([OH:22])=[O:21].Cl>N1C=CC=CC=1.O>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[N:25][O:24][CH2:23][C:20]([OH:22])=[O:21])[CH2:14][CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 286(Aminooxy)acetic acidHCID 313Hydrochloric AcidHCID 154869126-(2-Imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 54363749HCID 54363749, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 1.0 g (3.9 mmol) of 6-[2-(1H-1-imidazolyl)ethoxy]-1,2,3,4-tetrahydro-1-naphthalenone in 10 mL of pyridine was treated with 1.02 g (9.3 mmol) of carboxymethoxyamine×0.5 HCl and the solution heated at reflux for 2 days. The solution was diluted with H2O and extracted with EtOAc. On standing, the aqueous phase deposited a solid which was collected and dried. There was obtained 0.56 g (43% yield) of the product as a white solid, mp 193-195° C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 330 (M+H+).

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 2 days
  3. extractionextracted with EtOAc
  4. customwas collected
  5. customdried

Sources & evidence

ORD record
ord-e2f3ea0138f646ad959672103d956c89
Source dataset
uspto-grants-2001_07
Patent number
US06265422B1

Reaction notes

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