Hydroxylamine → HCID 23339651, compound

HRID 26816Notes

Reaction equation

HRID 26816 reaction equation
[C:1]1([NH:11][C:12]([CH2:14][C:15]([O:17]CC)=O)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:20][OH:21].Cl.NO.[Na]>CO>[C:1]1([NH:11][C:12]([CH2:14][C:15]([NH:20][OH:21])=[O:17])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 12547460Ethyl alpha-naphthylcarbamoylacetate

Product 1

HCID 23339651HCID 23339651, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

19.3 g (0.075 mol) of ethyl α-naphthylcarbamoylacetate are treated with a solution of hydroxylamine, prepared from 5.6 g (0.08 mol) of hydroxylamine hydrochloride and 3.68 g of sodium in 250 ml of methanol. After leaving the reactants in contact for 5 hours, the mixture is evaporated to dryness in vacuo, the residue is taken up in 400 ml of cold water, the solution is filtered over charcoal, and the product is precipitated cold with 3 N HCl, filtered off and washed with water. CRL 40,518 is obtained by recrystallisation from ethanol. Yield: 62%. Melting point: 184°-186° C. (with decomposition).

Workup

  1. customAfter leaving the reactants in contact for 5 hours
  2. customthe mixture is evaporated to dryness in vacuo
  3. filtrationthe solution is filtered over charcoal
  4. customthe product is precipitated cold with 3 N HCl
  5. filtrationfiltered off
  6. washwashed with water
  7. customCRL 40,518 is obtained by recrystallisation from ethanol

Sources & evidence

ORD record
ord-34e19f4dc75d49fc88b2096e844cd957
Source dataset
uspto-grants-1979_04
Patent number
US04151300

Reaction notes

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