Sodium Hydroxide → N-Hydroxy-3-(2-quinolinyl)propanamide

HRID 655880Notes

Reaction equation

HRID 655880 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[CH2:11][CH2:12][C:13]([O:15]C)=O.Cl.[NH2:18][OH:19].[OH-].[Na+].OP([O-])(O)=O.[K+]>CO.O>[OH:19][NH:18][C:13](=[O:15])[CH2:12][CH2:11][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 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 516951Monobasic potassium phosphateHCID 59134937Methyl 3-(2-quinolinyl)propanoate

Product 1

HCID 10059156N-Hydroxy-3-(2-quinolinyl)propanamideYield 48.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-(2-quinolinyl)propanoate (4) (0.111 g, 0.52 mmol) and hydroxylamine hydrochloride (0.144 g, 2.07 mmol) in methanol (3 ml), a solution of NaOH (0.165 g, 4.13 mmol) in water (0.5 ml) was added and the resulting mixture was stirred at room temperature for 30 minutes. The pH of the reaction medium was brought to 7 with saturated KH2PO4, the mixture was extracted with ethyl acetate (3×−15 ml), and the combined extracts were dried (Na2SO4). The solvent was evaporated under reduced pressure, the residue was washed with small amount of ethyl acetate and crystallized from acetonitrile to give the title compound (0.054 g, 48.1%). M.p. 159-160° C. 1H NMR (DMSO-d6, HMDSO), δ: 2.45-2.57 (m, 2H, overlapped with a signal of DMSO); 3.15 (t, J=7.2 Hz, 2H); 7.44 (d, J=8.4 Hz, 1H); 7.54 (ddd, J=8.2, 7.6, and 1.2 Hz, 1H); 7.71 (ddd, J=8.6, 7.0, and 1.4 Hz, 1H); 7.92 (d, J=8.6 Hz, 2H); 8.25 (d, J=8.4 Hz, 1H); 8.71 (s, 1H); 10.44 (s, 1H). HPLC analysis on Omnispher 5 C18: impurities ˜2.3% (column size 4.6×150 mm; mobile phase-5% acetonitrile+95% 0.1M phosphate buffer (pH 2.5); detector UV 230 nm; sample concentration 0.5 mg/ml; flow rate 1.5 ml/min). Anal. Calcd for C12H12N2O2 containing 2% of inorganic impurities: C, 65.32; H, 5.48; N, 12.70. Found, %: C, 65.42; H, 5.39; N, 12.43.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×−15 ml)
  2. dry with materialthe combined extracts were dried (Na2SO4)
  3. customThe solvent was evaporated under reduced pressure
  4. washthe residue was washed with small amount of ethyl acetate
  5. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-75c3fbbdc62e4b2ca25299fb6c5679c3
Source dataset
uspto-grants-2011_12
Patent number
US08071620B2

Reaction notes

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