Hydroxyamine hydrochloride → HCID 46918725, compound

HRID 403626Notes

Reaction equation

HRID 403626 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)C.Cl.[NH2:25][OH:26].C[O-].[Na+]>CO.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[OH:26][NH:25][C:4](=[O:3])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 66873467HCID 66873467, compound

Product 1

HCID 46918725HCID 46918725, compoundYield 43.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

6-Carbazol-9-ylhexanoic acid ethyl ester (14) (1.0 g, 3.2 mmol) and hydroxylamine hydrochloride (1.4 g, 19.4 mmol) were placed under argon and dissolved in 5 mL of methanol. To it was added a 25 wt. % sodium methoxide solution in methanol (5.6 g, 25.9 mmol) which resulted in the formation of a white precipitate. The reaction was stirred for 24 h at room temperature after which the reaction was diluted with ethyl acetate (20 mL) and saturated aqueous NaHCO3 (20 mL). The organic layer was isolated and the aqueous layer was further extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine (10 mL), dried with anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude extract was purified by HPLC to yield the title compound (0.41 g, 41%) as a white solid. 1H NMR (400 MHz, DMSO): δ 10.29 (s, 1H), 8.64 (s, 1H), 8.15 (d, 2H, J=7.7 Hz), 7.59 (d, 2H, J=8.2 Hz), 7.46 (m, 2H), 7.19 (m, 2H), 4.37 (t, 2H, J=7.1 Hz), 1.90 (t, 2H, J=7.3 Hz), 1.76 (m, 2H), 1.51 (m, 2H), 1.30 (m, 2H). 13C NMR (100 MHz, DMSO): δ 169.4, 140.4, 126.1, 122.4, 120.7, 119.1, 109.6, 42.6, 32.6, 28.7, 26.6, 25.3. ESI-HRMS (m/z): [M+H]+ calcd. for C18H20N2O2, 297.1598. found, 297.1591. Analytical HPLC: Purity=99%, tR=10.54 min, Method A.

Workup

  1. customresulted in the formation of a white precipitate
  2. customThe organic layer was isolated
  3. extractionthe aqueous layer was further extracted with ethyl acetate (2×10 mL)
  4. washThe combined organic layers were washed with brine (10 mL)
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. extractionThe crude extract
  9. customwas purified by HPLC

Sources & evidence

ORD record
ord-30c0975aa2444991b2488af722f38e14
Source dataset
uspto-grants-2014_06
Patent number
US08748451B2

Reaction notes

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