Ammonium Hydroxide → HCID 69706529, compound

HRID 392904Notes

Reaction equation

HRID 392904 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[N:17])([CH3:4])([CH3:3])[CH3:2].[OH-].[NH4+].[H][H]>[Ni].CO>[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[CH2:16][NH2:17])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 22661834HCID 22661834, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69706529HCID 69706529, compoundYield 630.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney nickel (˜0.5 g) was added to a solution of 2-cyano-4-chlorophenoxy acetic acid-t-butyl ester (560 mg, 0.21 mmol) in methanol (25 mL) containing 1 mL of sat. ammonium hydroxide. The mixture was placed under 40 psi of hydrogen and shaken for two hours. The mixture was filtered and concentrated. The residue was partitioned between 1 N HCl and ether. The layers were separated and the aqueous layer was re-extracted with ether. The aqueous layer was basified to ˜pH with K2CO3 solution and extracted with ether (3×). The combined organic layers were dried (MgSO4), filtered and concentrated to afford 360 mg of the title compound as an oil. MS 272 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.22 (s, 1H); 7.12 (d, 1H, J=8.7 Hz); 6.61 (d, 1H, J=8.7 Hz); 4.5 (s, 2H); 3.85 (s, 2H); 2.62 (bs, 2H); 1.41 (s, 9H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was partitioned between 1 N HCl and ether
  4. customThe layers were separated
  5. extractionthe aqueous layer was re-extracted with ether
  6. extractionextracted with ether (3×)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-bf1e4c46c7d04b6ea06b062db03b5cff
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Reaction notes

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