Acetic Acid → HCID 68417859, compound

HRID 733512Notes

Reaction equation

HRID 733512 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15].C(O)(=O)C.N#N>CO.[Pd]>[C:3]([OH:18])(=[O:2])[CH3:4].[NH2:11][CH2:10][C:8]1[CH:7]=[CH:6][C:5]([O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:4]([CH:9]=1)[C:3]([O:2][CH3:1])=[O:18]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 947NitrogenHCID 57841318HCID 57841318, compound

Product 1

HCID 68417859HCID 68417859, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl-5-cyano-2-(2-methoxy-2-oxoethoxy)benzoate (5 g, 0.02 mol) in methanol (1 L) was added glacial acetic acid (1.1 g, 0.02 mol) and passed N2 for 30 min. To this was added Pd/C (1.5 g, 35%) and hydrogenated under 2.5 Kg of pressure for 24 h. The reaction mixture was filtered and filtrate concentrated under vacuum (temp. 38° C. under N2). To the crude residue was added 100 mL of EtOAc and again removed under vacuum at same temp. The solid was treated with 100 mL EtOAc, stirred for 2 h, filtered and dried to give the title compound as a white powder (2.25 g, 35%). TLC: chloroform/methanol, 9:1, Rf: 0.15

Workup

  1. customfor 30 min
  2. filtrationThe reaction mixture was filtered
  3. concentrationfiltrate concentrated under vacuum (temp. 38° C. under N2)
  4. additionTo the crude residue was added 100 mL of EtOAc
  5. customagain removed under vacuum at same temp
  6. additionThe solid was treated with 100 mL EtOAc
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-98326eb40ead43c9a9bb44b5140912db
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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