Hydrochloric Acid → (E)-N-Hydroxy-3-(2-quinolinyl)-2-propenamide

HRID 655878Notes

Reaction equation

HRID 655878 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[C:13]([OH:15])=O.C(N(CC)CC)C.Cl.[NH2:24][OH:25].Cl>CN(C)C=O.O>[OH:25][NH:24][C:13](=[O:15])/[CH:12]=[CH:11]/[C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 7129193-(2-Quinolinyl)-2-propenoic acid

Product 1

HCID 10081950(E)-N-Hydroxy-3-(2-quinolinyl)-2-propenamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-(2-quinolinyl)-2-propenoic acid (2) (0.4 g, 2.0 mmol) in dry dimethylformamide (3 ml), at ice bath temperature (˜0° C.), under an atmosphere of argon, N,N′-carbonyldiimidazole (0.65 g, 4.0 mmol) was added over 15 minutes and the reaction mixture was stirred at this temperature for 2 hours. Triethylamine (0.85 ml, 6.0 mmol), followed by hydroxylamine hydrochloride (0.42 g, 6.0 mmol), were added to the reaction, and the obtained mixture was stirred at ice bath temperature for 1 hour, and then at room temperature overnight. The reaction mixture was poured into water (30 ml), acidified with 1 N HCl to pH 5 and extracted with ethyl acetate (3×40 ml). The combined extracts were washed with water (50 ml), brine (20 ml), and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silica gel with acetonitrile-water (20:1) as eluent to give the title compound as white crystals. M.p. 159.5-160.5° C. 1H NMR (DMSO-d6, HMDSO), δ: 7.12 (1H, d, J=16.0 Hz); 7.49-8.18 (6H, m); 8.44 (1H, d, J=8.0 Hz); 10.13 (2H, br s). HPLC analysis on Symmetry C8 column: impurities 2.0% (column size 3.9×150 mm; mobile phase acetonitrile-0.1M phosphate buffer, pH 2.5, 20:80; detector UV 254 nm; flow rate 1.2 ml/min; sample concentration 0.5 mg/ml). Anal. Calcd for C12H10N2O2*H2O: C, 62.06; H, 5.21; N, 12.06. Found, %: C, 61.95; H, 4.91; N, 12.07.

Workup

  1. additionwere added to the reaction
  2. stirringthe obtained mixture was stirred at ice bath temperature for 1 hour
  3. customat room temperature
  4. customovernight
  5. extractionextracted with ethyl acetate (3×40 ml)
  6. washThe combined extracts were washed with water (50 ml), brine (20 ml)
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was evaporated
  9. customthe residue was chromatographed on silica gel with acetonitrile-water (20:1) as eluent

Sources & evidence

ORD record
ord-146923fc391b4c748396f6e8ee147da9
Source dataset
uspto-grants-2011_12
Patent number
US08071620B2

Reaction notes

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