Ethyl Acetate → HCID 68982189, compound

HRID 1930309Notes

Reaction equation

HRID 1930309 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([F:9])[C:6]([N+:10]([O-])=O)=[CH:5][C:4]=1[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[CH:2].CCOC(C)=O>CO.[Pd]>[NH2:10][C:6]1[C:7]([F:9])=[CH:8][C:3]([CH2:1][CH3:2])=[C:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 86620162HCID 86620162, compound

Product 1

HCID 68982189HCID 68982189, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl 2-(2-ethynyl-4-fluoro-5-nitrophenyl)acetate (160 mg, 0.64 mmol) was dissolved in MeOH (5 mL) and EtOAc (5 mL) and then Pd—C (20 mg) was added. The reaction mixture was shaken in a Parr hydrogenator (46 psi) overnight at RT. The reaction mixture was filtered, washed with methanol, and concentrated to obtain ethyl 2-(5-amino-2-ethyl-4-fluorophenyl)acetate (135 mg, 93% yield). MS (ESI) m/z: 226.2 (M+H+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-34d3bedf34514cb785d5f5e924348b5e
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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