Hydroxyamine hydrochloride → A-967079

HRID 514662Notes

Reaction equation

HRID 514662 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](\[CH3:14])/[C:10](=O)[CH2:11][CH3:12])=[CH:4][CH:3]=1.Cl.[NH2:16][OH:17]>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](\[CH3:14])/[C:10](=[N:16]\[OH:17])/[CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 68629219HCID 68629219, compound

Product 1

HCID 60150207A-967079Yield 7.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Example 1D (1.96 g, 10.2 mmol) in pyridine (40 mL) was added hydroxylamine hydrochloride (1.06 g, 15.3 mmol) in one portion. The reaction was stirred at ambient temperature for 12 hr, and then concentrated in vacuo. The residue was partitioned between EtOAc and 1M aq HCl. The separated organic phase was washed with 1M aq HCl and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by chromatography on silica gel (Analogix Intelliflash 280; 5% to 30% EtOAc/hexanes; SF40-115 g column) and the late eluting component was isolated to afford the title compound as a white solid (0.16 g, 7.6% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 10.34 (s, 1H), 7.44-7.34 (m, 2H), 7.25-7.15 (m, 2H), 6.36 (s, 1H), 2.36 (q, J=7.4 Hz, 2H), 1.98 (d, J=1.5 Hz, 3H), 1.05 (t, J=7.4 Hz, 3H). MS (DCI+): 208 (M+H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between EtOAc and 1M aq HCl
  3. washThe separated organic phase was washed with 1M aq HCl and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by chromatography on silica gel (Analogix Intelliflash 280; 5% to 30% EtOAc/hexanes; SF40-115 g column)
  8. customthe late eluting component was isolated

Sources & evidence

ORD record
ord-1e85ce518afc419bbe086a22f23853ec
Source dataset
uspto-grants-2015_08
Patent number
US09108905B2

Reaction notes

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