Nitrogen → HCID 22720608, compound

HRID 1582438Notes

Reaction equation

HRID 1582438 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:4]=1[CH2:12][C:13](=O)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].N#N.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[CH:12]=[C:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:9]2

Participants

6

Reactant 3

HCID 947NitrogenHCID 2723923Ammonium formateHCID 22720510HCID 22720510, compound

Product 1

HCID 22720608HCID 22720608, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(Chart A, Step 2): A solution of ethyl 4-(2-methoxy-6-nitrophenyl)-3-oxobutanoate (10.6 g, 37.5 mmol) in MeOH (350 mL) is purged with N2, and treated with 10% Pd/C (1.10 g) turning the yellow solution black. The suspension is treated with ammonium formate (27.4 g, 43.5 mmol) with a slight exotherm and evolution of H2. After 15 minutes, the reaction mixture is filtered through a pad of celite, and concentrated. The residue is diluted with water and extracted 3 times with ethyl acetate. The combined organics are washed with brine, dried over NaSO4, filtered, and concentrated to give 9.4 g of crude material which is combined with the crude material from a previous 1.5 mmol reaction. The crude material is purified by LC (25% ethyl acetate/heptane) to give 8.08 g of substituting ethyl 2-(4-methoxy-1H-indol-2-yl)acetate as an oil that solidifies overnight. IR (liq.) 3389, 1730, 1617, 1594, 1510, 1438, 1367, 1287, 1250, 1217, 1167, 1151, 1097, 1030, 767 cm−1.

Workup

  1. filtrationthe reaction mixture is filtered through a pad of celite
  2. concentrationconcentrated
  3. additionThe residue is diluted with water
  4. extractionextracted 3 times with ethyl acetate
  5. washThe combined organics are washed with brine
  6. dry with materialdried over NaSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give 9.4 g of crude material which
  10. customThe crude material is purified by LC (25% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-bb0b57df2a8149d583ab0ec35619aace
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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