Ammonium formate → HCID 68567953, compound

HRID 747606Notes

Reaction equation

HRID 747606 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[CH:11]([C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:20])[OH:12])([O-])=O.C([O-])=O.[NH4+]>CO.[Pt]=O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[CH:11]([C:13]1[C:14]([Cl:20])=[CH:15][CH:16]=[CH:17][C:18]=1[Cl:19])[OH:12]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68568445HCID 68568445, compound

Product 1

HCID 68567953HCID 68567953, compoundYield 38.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To 3.9 g of (2-nitro-5-chlorophenyl)(2,6-dichlorophenyl)methanol dissolved in 37 ml of methanol are added 5.25 g of ammonium formate and 0.374 g of platinum oxide. The mixture is left for 5 hours at room temperature and then heated at 50° C. for 18 hours. The resulting mixture is filtered through Celite and the filtrate is concentrated. The residue is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a 90/10 (v/v) cyclohexane/ethyl acetate mixture to give 1.378 g of the expected product.

Workup

  1. filtrationThe resulting mixture is filtered through Celite
  2. concentrationthe filtrate is concentrated
  3. washwashed with water
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on a column of silica gel
  7. washeluting with a 90/10 (v/v) cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-2ce4ccaecf6b4af68f0700f2ab79310d
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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