Ethyl Acetate → HCID 28395198, compound

HRID 555397Notes

Reaction equation

HRID 555397 reaction equation
[N+:1]([C:4]1[C:5]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.C(OCC)(=O)C>[Pd].CO>[F:20][C:17]([F:18])([F:19])[C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:5]1[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 288110HCID 288110, compound

Product 1

HCID 28395198HCID 28395198, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3a (20 g, 70 mmol) in a 1:4 mixture of ethyl acetate and methanol (250 mL) was added palladium on charcoal (10% wt, 1.0 g, 0.90 mmol), and the mixture was stirred under an atmosphere of hydrogen. After 3 h, the solution was filtered over Celite® and the resulting solution was concentrated. 3b was recrystallized from ethyl acetate to afford 17.5 g of white crystals (97% yield). [M+H]+=255.20.

Workup

  1. filtrationthe solution was filtered over Celite®
  2. concentrationthe resulting solution was concentrated
  3. custom3b was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f939664877ee47ffbe779dabb68a45c1
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

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