Hydroxyamine hydrochloride → HCID 86748111, compound

HRID 2225854Notes

Reaction equation

HRID 2225854 reaction equation
Cl.[NH2:2][OH:3].[CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[O:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=O)[C:25]([OH:27])=[O:26])=[CH:20][CH:19]=1>[OH-].[Na+].CN(C)C=O>[OH:3][N:2]=[C:24]([C:21]1[CH:22]=[CH:23][C:18]([O:17][CH2:16][CH2:15][O:14][C:5]2[CH:6]=[CH:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:4]=2)=[CH:19][CH:20]=1)[C:25]([OH:27])=[O:26]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 19004267HCID 19004267, compound

Product 1

HCID 86748111HCID 86748111, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of hydroxylamine hydrochloride (0.089 g) in 1N sodium hydroxide solution (1.3 mL) was added to a solution of 4-[2-(2-naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid (0.291 g) in dimethylformamide and the mixture was heated on a steam bath till all the solids dissolved. The reactants were maintained in solution by intermittent heating over 2 hours, then the mixture was stirred at room temperature overnight. The formed precipitate was filtered off, then the filtrate was diluted with water and adjusted to pH 2 by the addition of dilute hydrochloric acid solution. The resulting solid was recovered by filtration and dried in vacuo to furnish 0.164 g of (Z)-alpha-(hydroxyimino-4-[2-(2-naphthalenyloxy)ethoxy]benzeneacetic acid, mp 178°-179° C.

Workup

  1. temperaturethe mixture was heated on a steam bath till all the solids
  2. dissolutiondissolved
  3. temperatureThe reactants were maintained in solution by intermittent
  4. temperatureheating over 2 hours
  5. filtrationThe formed precipitate was filtered off
  6. additionthe filtrate was diluted with water
  7. additionadjusted to pH 2 by the addition of dilute hydrochloric acid solution
  8. filtrationThe resulting solid was recovered by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-77bfa00fff224bb0a6796afafbdca479
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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