Ethanol → HCID 73178202, compound

HRID 1794726Notes

Reaction equation

HRID 1794726 reaction equation
C([O-])(=O)C.[Na+].[O:6]1[C:10]2([CH2:15][CH2:14][N:13]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[O:9][CH2:8][CH2:7]1.Cl.[NH2:25][OH:26].C(O)C>O>[O:6]1[C:10]2([CH2:15][CH2:14][N:13]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=[N:25][OH:26])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[O:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 27643354-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)benzaldehyde

Product 1

HCID 73178202HCID 73178202, compoundYield 118.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
70 °C

Procedure

A solution of sodium acetate (6.64 g, 60.72 mmol) in water (10 mL) was added into a mixture of 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzaldehyde (5.0 g, 20.24 mmol) benzaldehyde (Taylor, E. C., Skotnicki, J. S. Synthesis, 1981, 606), hydroxylamine hydrochloride (4.22 g, 60.72 mmol), ethyl alcohol (300 mL), and water (50 mL). The mixture: was stirred at 70° C. for 10 hours, then poured into water and extracted with ethyl acetate. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/ethyl acetate 2/1) gave a white solid (6.3 g, 90% yield); mp 151–152° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.63 (m, 4H), 3.35 (m, 4H), 3.90 (s, 4H), 6.96 (m, 2H), 7.40 (m, 2H), 7.96 (s, 1H), 10.75 (s, 1H); MS (ES) m/z: 263 (MH+); Anal. Calcd. for C14H18N2O3: C, 64.11; H, 6.92; N, 10.68. Found: C, 64.24; H, 6.81; N, 10.64.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography (hexanes/ethyl acetate 2/1)

Sources & evidence

ORD record
ord-2214e265becc47c394b8a434c858db23
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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