HCID 18512076, compound → HCID 86586222, compound

HRID 1370778Notes

Reaction equation

HRID 1370778 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[CH2:19]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[C:10]=1[CH3:18])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 18512076HCID 18512076, compound

Product 1

HCID 86586222HCID 86586222, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

The product from Example 2A (3.4 g, 16.2 mmoles) in acetic acid (20 mL) was treated with zinc powder (2.68 g, 41 mmoles, purchased from Aldrich) and stirred for 48 hours. An additional portion of zinc (1.0 g, 15.3 mmoles) was added and stirring continued for 4 hours. The reaction was filtered through a pad of Celite with CH2Cl2 and concentrated. Purification by flash chromatography (silica gel, 4:1 hexanes:ethyl acetate) provided the title compound as a yellow solid (1.98 g, 64%).

Workup

  1. stirringstirring
  2. waitcontinued for 4 hours
  3. filtrationThe reaction was filtered through a pad of Celite with CH2Cl2
  4. concentrationconcentrated
  5. customPurification by flash chromatography (silica gel, 4:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-494fa32753c541be822d4d9461481ba2
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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