Hydrochloric Acid → HCID 86035754, compound

HRID 495127Notes

Reaction equation

HRID 495127 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:32][N:33]([CH3:38])[CH2:34][CH2:35][CH2:36]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C([Cl:56])(=O)C.Cl>C1COCC1.O1CCOCC1.CO>[ClH:56].[CH3:32][N:33]([CH3:38])[CH2:34][CH2:35][CH2:36][O:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:5][C:4](=[O:12])[CH:3]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 11776TriphenylphosphineHCID 766463-(Dimethylamino)-1-propanolHCID 5363146Diisopropyl azodicarboxylateHCID 546829304-Hydroxycoumarin

Product 1

HCID 86035754HCID 86035754, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Hydroxycoumarin (3.0 mmol, 0.487 g) is dissolved in 10 mL of THF. Triphenylphosphine (3.15 mmol, 0.825 g) and 3-dimethylamino-propan-1-ol (3.15 mmol, 0.372 mL) is added and the solution is cooled to 0° C. DIAD (3.30 mmol, 0.647 g) is added dropwise at 0° C. The reaction is stirred 30 min. at 0° C then is allowed to warm to ambient temperature and is stirred overnight. The solvent is evaporated under reduced pressure, and a solution of anhydrous HCl/MeOH (prepared by adding ˜5 mL acetyl chloride dropwise to 100 mL MeOH) is added to the residue. Alternatively 4M HCl in dioxane may be used. The solvent is removed under reduced pressure and the residue is treated with Et2O. The resulting solid is filtered, is washed with Et2O, and is dried to afford the title compound as the hydrochloric acid salt (0.485g, 57%). 1H NMR (DMSO-d6, 300 MHz) δ 10.35 (1H, br s), 7.90 (1H, dd, J=1.25, 7.75 Hz), 7.68 (1H, m), 7.41 (2H, m), 5.92 (1H, s), 4.32 (2H, t, J=5.75 Hz), 3.27 (2H, m), 2.80 (6H, s), 2.25 (2H, m); MS (ESI, Pos.) calcd for C14H17NO3 m/z [M+H]=248.1, found 248.1.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringis stirred overnight
  3. customThe solvent is evaporated under reduced pressure
  4. customa solution of anhydrous HCl/MeOH (prepared
  5. additionis added to the residue
  6. customThe solvent is removed under reduced pressure
  7. additionthe residue is treated with Et2O
  8. filtrationThe resulting solid is filtered
  9. washis washed with Et2O
  10. customis dried

Sources & evidence

ORD record
ord-2285fefadf2b471a8d83e66cf2d516ed
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

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