Hydroxyamine hydrochloride → HCID 86671719, compound

HRID 403640Notes

Reaction equation

HRID 403640 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:7][CH:6]=1.Cl.[NH2:27][OH:28].C[O-].[Na+]>CO.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[CH:23]1[C:24]2[N:12]([CH2:11][C:8]3[CH:9]=[CH:10][C:5]([CH2:4][C:3]([NH:27][OH:28])=[O:2])=[CH:6][CH:7]=3)[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]=2[CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 66873124HCID 66873124, compound

Product 1

HCID 86671719HCID 86671719, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

(4-Carbazol-9-ylmethylphenyl)acetic acid methyl ester (25) (0.25 g, 0.8 mmol) and hydroxylamine hydrochloride (0.32 g, 4.6 mmol) were placed under argon and dissolved in 5 mL of methanol. To it was added a 25% sodium methoxide solution in methanol (1.33 g, 6.2 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 sodium bicarbonate (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 (Na2SO4) and concentrated in vacuo. The crude extract was purified by HPLC to yield the title compound (100 mg, 40%) as a white solid. 1H NMR (400 MHz, DMSO): δ 10.57 (s, 1H), 8.73 (s, 1H), 8.17 (d, 2H, J=7.7 Hz), 7.61 (d, 2H, J=8.2 Hz), 7.42 (t, 2H, J=7.5 Hz), 7.20 (t, 2H, J=7.4 Hz), 7.11 (m, 4H), 5.62 (s, 2H), 3.18 (s, 2H). 13C NMR (100 MHz, CD3OD): δ 168.9, 140.2, 136.1, 133.8, 128.5, 126.0, 125.0, 122.5, 119.3, 118.4, 108.3, 45.0, 38.4. ESI-HRMS (m/z): [M+H]+ calcd. for C21H18N2O2, 331.1441. found, 331.1445. Analytical HPLC: Purity=99%, tR=6.82 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 (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. extractionThe crude extract
  8. customwas purified by HPLC

Sources & evidence

ORD record
ord-38a6e91c0c97403f960b45616a93ee0e
Source dataset
uspto-grants-2014_06
Patent number
US08748451B2

Reaction notes

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