HCID 53974214, compound → HCID 10378485, compound

HRID 1684630Notes

Reaction equation

HRID 1684630 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[C:17](=[O:29])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=1)C1C=CC=CC=1.[H][H]>[Pd].O1CCCC1.CO>[NH2:26][C:22]1[CH:21]=[C:20]([CH2:19][CH2:18][C:17]([C:10]2[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:9]=2[OH:8])=[O:29])[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 2

HCID 53974214HCID 53974214, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10378485HCID 10378485, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 15.0 g (0.039 mole) of the title product from Example 120 and 1.5 g 5% palladium on charcoal in 300 ml tetrahydrofuran and 200 ml absolute methanol was shaken in a Parr hydrogenator under 10 psi hydrogen at ambient temperature for 3 hours. The reaction mixture was filtered through Celite and the filtrate was evaporated in vacuo to yield an oil. Column chromatography of the oil on silica gel eluting with ethyl acetate: hexanes (1:2, v/v) gave 9.42 g (90%) of the title product as an oil; 1H NMR (CDCl3): δ2.98 (t, J=8 Hz, 2H); 3.28 (t, J=8 Hz, 2H); 3.65 (s, br, 2H); 3.77 (s, 3H); 6.65 (m, 3H); 6.93 (d, J=9 Hz, 1H); 7.10 (m, 3H); 11.95 (s, 1H). Analysis calculated for C16H17NO3 : C, 70.83; H, 6.32; N, 5.16. Found: C, 70.51; H, 6.30; N, 4.97.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe filtrate was evaporated in vacuo
  3. customto yield an oil

Sources & evidence

ORD record
ord-b6b5c96b962f45d68ee40eb356e8e002
Source dataset
uspto-grants-1997_06
Patent number
US05641789

Reaction notes

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