Hydroxyamine hydrochloride → methyl (8E)-8-hydroxyimino-6,7-dihydro-5H-naphthalene-2-carboxylate

HRID 733517Notes

Reaction equation

HRID 733517 reaction equation
O=[C:2]1[C:11]2[CH:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>CO>[OH:18]/[N:17]=[C:2]1\[CH2:3][CH2:4][CH2:5][C:6]2[CH:7]=[CH:8][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:11]\1=2

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 10987358Methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

Product 1

HCID 57841419methyl (8E)-8-hydroxyimino-6,7-dihydro-5H-naphthalene-2-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate (10 g, 0.048 mol) in MeOH (100 ml) was added hydroxylamine hydrochloride (5 g, 0.07 mol), followed by sodium acetate (6 g, 0.072 mol). The reaction mixture was stirred at rt for 1 h and heated to 50° C. for 15 h. The solvent was removed under vacuum and the residue was diluted with water. The product was extracted with EtOAc (2×150 ml), dried and evaporated to yield 10 g (93%) of the titled compound as a solid. TLC-Chloroform/MeOH (9/1), Rf=0.3.

Workup

  1. temperatureheated to 50° C. for 15 h
  2. customThe solvent was removed under vacuum
  3. additionthe residue was diluted with water
  4. extractionThe product was extracted with EtOAc (2×150 ml)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-42ee40df2b9f4f66af0d51910d348a7b
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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