Hydroxyamine hydrochloride → HCID 86750579, compound

HRID 976348Notes

Reaction equation

HRID 976348 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[CH:9]([C:11]1[C:12]([O:25][CH2:26][C:27]#[C:28][C:29]2[CH:39]=[CH:38][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][CH:30]=2)=[CH:13][C:14]2[C:15]([CH3:24])([CH3:23])[CH2:16][CH2:17][C:18]([CH3:22])([CH3:21])[C:19]=2[CH:20]=1)=O>CO>[OH:3][N:2]=[CH:9][C:11]1[C:12]([O:25][CH2:26][C:27]#[C:28][C:29]2[CH:39]=[CH:38][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][CH:30]=2)=[CH:13][C:14]2[C:15]([CH3:24])([CH3:23])[CH2:16][CH2:17][C:18]([CH3:22])([CH3:21])[C:19]=2[CH:20]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 19967155HCID 19967155, compound

Product 1

HCID 86750579HCID 86750579, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

0.2 g of hydroxylamine hydrochloride and 0.26 g of sodium acetate were added to 15 ml of a solution of 0.51 g of ethyl 4-[3-(3-formyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoxy)-1-propynyl]benzoate in methanol at room temperature. The obtained mixture was stirred at 50° C. for 11 hours and distilled to remove the methanol, followed by the addition thereto of 20 ml of water. The obtained mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by silica gel chromatography (developer: 30% diethyl ether/n-hexane) to give 0.33 g of the title compound as a pale-yellow oil. 1H-NMR (400 MHz, CDCl3) δ(ppm); 1.28(s, 6H), 1.30(s, 6H), 1.36(t, J=7.2 Hz, 3H), 1.68(brs, 4H), 4.36(q, J=7.2 Hz, 2H), 4.94(s, 2H), 7.04(s, 1H), 7.47(d, J=8.4 Hz, 2H), 7.68(s, 1H), 7.98(d, J=8.4 Hz, 2H), 8.50(s, 1H)

Workup

  1. distillationdistilled
  2. customto remove the methanol
  3. additionfollowed by the addition
  4. extractionThe obtained mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with a saturated aqueous solution of common salt
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue was purified by silica gel chromatography (developer: 30% diethyl ether/n-hexane)

Sources & evidence

ORD record
ord-4913f01363ee464eae136557d398580a
Source dataset
uspto-grants-1997_03
Patent number
US05612356

Reaction notes

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