Water → 4-(6-Chloro-2-oxo-2H-1-benzopyran-4-yl)-butyramide

HRID 495152Notes

Reaction equation

HRID 495152 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=[O:11])[CH:8]=[C:7]([CH2:12][CH2:13][CH2:14][C:15]#[N:16])[C:6]=2[CH:17]=1.[OH2:18]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=[O:11])[CH:8]=[C:7]([CH2:12][CH2:13][CH2:14][C:15]([NH2:16])=[O:18])[C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 962WaterHCID 118174844-(6-Chloro-2-oxo-2H-1-benzopyran-4-yl)-butyronitrile

Product 1

HCID 113914604-(6-Chloro-2-oxo-2H-1-benzopyran-4-yl)-butyramideYield 93%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-(6-Chloro-2-oxo-2H-1-benzopyran-4-yl)-butyronitrile (100 mg, 0.4 mmol) is dissolved in conc. H2SO4 (2 mL) and is stirred for 4 hrs. Ice and then H2O (20 mL) is added to the reaction mixture, and the resulting precipitate is filtered and is washed with H2O and Et2O. The solid is dried in vacuo to give the title compound (100 mg, 93%) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 7.98 (1H, d, J=2 Hz), 7.68 (1H, dd, J=2, 9 Hz), 7.47 (1H, d, J=9 Hz), 7.32 (1H, broad s), 6.83 (1H, broad s), 6.43 (1H, s), 2.79 (2H, t, J=7 Hz), 2.20 (2H, t, J=7 Hz), 1.82 (2H, q, J=7 Hz); LCMS (MeCN—H2O, Luna 3μ C18(2) 30×4.6 mm) m/z (ES, Pos) calc. for C13H12ClNO3 m/z [M+H]=266, found 266.

Workup

  1. filtrationthe resulting precipitate is filtered
  2. washis washed with H2O and Et2O
  3. customThe solid is dried in vacuo

Sources & evidence

ORD record
ord-538f78f6e29e4d229a3d24555f34b414
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

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