Hydroxyamine hydrochloride → HCID 18623289, compound

HRID 1860534Notes

Reaction equation

HRID 1860534 reaction equation
Cl.NO.[Na].C[O:6][C:7](=[O:23])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22].C[O-].[Na+]>CO>[O:22]=[C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:20][CH2:21][CH:12]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]([OH:23])=[O:6]

Participants

6

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 11425452HCID 11425452, compound

Product 1

HCID 18623289HCID 18623289, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a solution of 5.0 g (22.9 mmol) 1-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester (1a) (Pradeep, K., and Saravanan, K., Tetrahedron 54 (1998) 2161-2168) and 5.79 g ethyl-5-bromo-pentanoate (27.7 mmol) in 10 mL ethanol at reflux is added a freshly prepared solution of 0.53 g sodium in 15 mL ethanol. After 10 h at reflux enough water is added for the precipitate to dissolve. The solvent is evaporated, the residue is dissolved in a solution of 3.85 g KOH in 7 mL MeOH and 5 mL H2O and refluxed for another 10 h. After cooling the solution is poured into 25 mL ice-cold 4N HCl and extracted with CH2Cl2. Evaporation of the solvent leaves a residue of crude 5-(1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-pentanoic acid (1b) which is dissolved in 100 mL MeOH. A few drops of H2SO4 are added and the solution is refluxed over night. After addition of some sodiumbicarbonate-solution the solvent is evaporated and the residue is subjected to column-chromatography yielding 1.9 g methyl-(5-(1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-pentanoate) (1c). To a solution of 1.6 g (23 mmol) hydroxylamine hydrochloride in 40 mL MeOH is added 15 mL of a solution of 0.8 g (35 mmol) of sodium in 30 mL of MeOH. To this, a solution of 3.0 g (11.5 mmol) methyl-(5-(1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-pentanoate) (1c) in 20 mL MeOH is added, followed by the remaining 15 mL of the sodium methylate solution. After stirring for 6 h at rt the solvent is evaporated, acidified with 2N HCl and extracted with CH2Cl2. After evaporation the residue is purified by column-chromatography yielding 2.2 g of the title compound as an oil, MS (APCI): 260.1 (M−1).

Workup

  1. customis evaporated
  2. extractionextracted with CH2Cl2
  3. customAfter evaporation the residue
  4. customis purified by column-chromatography

Sources & evidence

ORD record
ord-dbc46ab83014449991a063d76ec5d310
Source dataset
uspto-grants-2003_03
Patent number
US06531472B2

Reaction notes

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