HCID 11531559, compound → HCID 11715743, compound

HRID 2243235Notes

Reaction equation

HRID 2243235 reaction equation
ClC1C=CC=C(Cl)C=1C[O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:22])[CH:11]=[C:12]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[O:13]2)=[CH:8][CH:7]=1>CO.[Pd]>[OH:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:22])[CH:11]=[C:12]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[O:13]2)=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 11531559HCID 11531559, compound

Product 1

HCID 11715743HCID 11715743, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a mixture of 7-(2,6-dichlorobenzyloxy)-2-(morpholin-4-yl)-chromen-4-one (6.60 g, 16.2 mmol) (299) and 10% Pd/C (150 mg) was added methanol (150 ml), under nitrogen. The suspension was stirred under an atmosphere of hydrogen for 40 h. The catalyst was removed by filtration through Celite, washing with methanol. The solvent was removed by evaporation in vacuo to provide an off-white solid. This was treated with fresh catalyst, re-suspended in methanol under nitrogen and stirred under an atmosphere of hydrogen for a further 72 h. The catalyst was removed by filtration through Celite, washing with methanol. The filtrate was evaporated in vacuo and the crude product re-crystallised from methanol to provide 2.26 g (9.1 mmol, 57%) of the desired compound as a white solid. mp>250° C. (decomp). 1H NMR (200 Mhz, d6-DMSO) δ 3.78 (4H, m); 3.86 (4H, m); 6.15 (1H, s); 7.05-7.13 (2H, m); 7.93 (1H, d); 11.3 (1H, bs). ESMS m/z=247 (M+), 190, 105.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. washwashing with methanol
  3. customThe solvent was removed by evaporation in vacuo
  4. customto provide an off-white solid
  5. additionThis was treated with fresh catalyst
  6. stirringstirred under an atmosphere of hydrogen for a further 72 h
  7. customThe catalyst was removed by filtration through Celite
  8. washwashing with methanol
  9. customThe filtrate was evaporated in vacuo
  10. customthe crude product re-crystallised from methanol

Sources & evidence

ORD record
ord-4f3fb8fc53cd44cbaf71f5651f2a09ee
Source dataset
uspto-grants-2010_03
Patent number
US07674823B2

Reaction notes

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