Ethanol → HCID 23156963, compound

HRID 2110110Notes

Reaction equation

HRID 2110110 reaction equation
[C:1]([O:4][NH:5][C:6]([C:8]1[O:12][C:11]([C:13]2[O:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24](=[NH:30])[NH:25]OC(=O)C)=[CH:20][CH:19]=3)=[CH:16][CH:17]=2)=[CH:10][CH:9]=1)=[NH:7])(=[O:3])[CH3:2].C(O)C>C(O)(=O)C.[Pd]>[C:1]([OH:4])(=[O:3])[CH3:2].[C:24]([C:21]1[CH:20]=[CH:19][C:18]([C:15]2[O:14][C:13]([C:11]3[O:12][C:8]([C:6]([NH2:7])=[NH:5])=[CH:9][CH:10]=3)=[CH:17][CH:16]=2)=[CH:23][CH:22]=1)(=[NH:25])[NH2:30]

Participants

5

Reactant 2

HCID 702EthanolHCID 178476700HCID 178476700, compound

Product 1

HCID 23156963HCID 23156963, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 7 (246 mg, 0.6 mmol) in glacial acetic acid (8 mL), and ethanol (20 mL) was added 10% palladium on carbon (60 mg). The mixture was placed in a Parr hydrogenation apparatus at 50 psi for 4 h at room temperature. The mixture was filtered through hyflo and the filter pad washed with water. The filtrate was evaporated under reduced pressure and the precipitate was collected and washed with ether to give 8a in 67% yield, mp 240-242° C. 1H NMR (D2O/DMSO-d6); δ 1.80 (s, 2×CH3), 7.06 (d, J=3.6 Hz, 1H), 7.11 (d, J=3.6 Hz, 1H), 7.36 (d, J=3.6 Hz, 1H), 7.39 (d, J=3.6 Hz, 1H), 7.89 (d, J=8.4 Hz, 2H), 7.98 (d, J=8.4 Hz, 2H). Calcd for C16H14N4O2-2.0AcOH-2.4H2O: C, 52.48; H, 5.87; N, 12.23. Found. C, 52.28; H, 5.49; N, 11.91.

Workup

  1. filtrationThe mixture was filtered through hyflo
  2. washthe filter pad washed with water
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe precipitate was collected
  5. washwashed with ether

Sources & evidence

ORD record
ord-d6133327fbba4d40ad1457c9ec256518
Source dataset
uspto-grants-2009_04
Patent number
US07517893B2

Reaction notes

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