Phosphorus oxychloride → HCID 86619239, compound

HRID 574047Notes

Reaction equation

HRID 574047 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]1[CH:4]=[C:5]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:6]2=[C:7]([CH:25]=1)[C:8](=[O:24])[N:9]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:10]3=[O:15].O=P(Cl)(Cl)[Cl:29]>CN(C=O)C>[Cl-:29].[C:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:9]1[C:8](=[O:24])[C:7]2[C:6]3[C:11](=[CH:12][CH:13]=[CH:14][C:5]=3[C:4]3[CH2:1][N+:2]([CH3:26])([CH3:3])[CH2:26][N:2]([CH3:1])[C:3]=3[CH:25]=2)[C:10]1=[O:15])([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 58301348HCID 58301348, compound

Product 1

HCID 86619239HCID 86619239, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 90 mg (0.25 mmol) of 6-(5-dimethylamino-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)hexanoic acid in 0.4 mL of DMF 0.09 ml of POCl3 were added dropwise at 40° C. The mixture was heated under stirring at 80° C. for 1.5 h, cooled to RT and poured into ice water. The product was precipitated with isopropyl alcohol and purified by column chromatography on reverse phase (PR-18, H2O-acetonitrile 5:1, v/v). Yield: 45 mg (40%) 4a. M.p. 186-188° C. 1H-NMR (200 MHz, DMSO-d6, δ, ppm): 8.39-7.82 (5H, arom), 5.17 s (2H, CH2), 4.85 s (2H, CH2), 4.04 t (2H, α-CH2, J 7.3 Hz), 3.65 s (3H, NCH3), 3.19 s (6H, +N(CH3)2), 1.94 t (2H, ε-CH2, J 7.3 Hz), 1.54 m (4H, β,γ-CH2 J 7.3 Hz), 1.26 m (2H, δ-CH2, J 7.3 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperaturecooled to RT
  3. customThe product was precipitated with isopropyl alcohol
  4. custompurified by column chromatography on reverse phase (PR-18, H2O-acetonitrile 5:1

Sources & evidence

ORD record
ord-4235151288fa4d47ae5623a5dfa9e54a
Source dataset
uspto-grants-2015_05
Patent number
US09034655B2

Reaction notes

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