HCID 19918495, compound → HCID 19918526, compound

HRID 1464827Notes

Reaction equation

HRID 1464827 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([O:19][CH2:20][CH3:21])[C:17]#[N:18])=[CH:11][C:10]=1[N+:22]([O-])=O)C1C=CC=CC=1>C(O)C.C(O)(=O)C.[Pd]>[NH2:22][C:10]1[CH:11]=[C:12]([CH2:15][CH:16]([O:19][CH2:20][CH3:21])[C:17]#[N:18])[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

5

Reactant 1

HCID 19918495HCID 19918495, compound

Product 1

HCID 19918526HCID 19918526, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 3-(4-benzyloxy-3-nitrophenyl)-2-ethoxypropanenitrile (0.54 g, 1.7 mmol) in ethanol (25 ml) and acetic acid (75 ml) containing 10% palladium on carbon (0.40 g) was hydrogenated at 45 psi for 1 hour. The catalyst was filtered and the solution concentrated. The residue was treated with 5% sodium bicarbonate (100 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with water (2×100 ml) and brine (100 ml), dried over sodium sulfate and concentrated. The product was isolated by column chromatography (silica gel, 2% methanol in chloroform) as a solid (0.20 g, m.p. 114°-115° C.)

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe solution concentrated
  3. additionThe residue was treated with 5% sodium bicarbonate (100 ml)
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. washThe combined extracts were washed with water (2×100 ml) and brine (100 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-311f80cabfa7480a985d4f4f94b1f5e0
Source dataset
uspto-grants-1994_04
Patent number
US05306726

Reaction notes

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