Hydrochloric Acid → HCID 178424859, compound

HRID 510384Notes

Reaction equation

HRID 510384 reaction equation
CO[CH:3](OC)/[C:4](=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[CH3:15])/[C:5]#[N:6].CC1C(C)=CC=CC=1CC(C(OC)OC)C#N.O.[NH2:36][NH2:37].Cl>CO.C(O)C.[Pd]>[CH3:15][C:9]1[C:10]([CH3:14])=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][C:4]1[C:5]([NH2:6])=[N:36][NH:37][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 86724875(2E)-2-[bis(methyloxy)methyl]-3-(2,3-dimethylphenyl)-2-propenenitrileHCID 867248762-[(2,3-Dimethylphenyl)methyl]-3,3-bis(methyloxy)propanenitrile

Product 1

HCID 178424859HCID 178424859, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

The suspension of (2E)-2-[bis(methyloxy)methyl]-3-(2,3-dimethylphenyl)-2-propenenitrile (1.55 g, 9.2 mmol) and 10% Pd/C (36 mg, 0.33 mmol) in methanol (25 mL) was hydrogenated using the Parr shaker (23° C., 50 bar) overnight. The catalyst was removed by filtration. Concentration of filtrate gave desire product. (0.26 g, 17%). To a solution of 2-[(2,3-dimethylphenyl)methyl]-3,3-bis(methyloxy)propanenitrile (257 mg, 1.1 mmol) and hydrazine monohydrate (55.1 mg, 1.1 mmol) in ethanol (15 ml) stirred under nitrogen at room temperature was added a solution of 36% HCl (558 mg, 5.51 mmol) dropwise. The reaction mixture was stirred at 100° C. for overnight. Reaction mixture was concentrated and dissolved with ethyl acetate (30 mL) and water (10 mL). pH of aqueous layer was adjusted to 8˜9. Two layers were separated. Organic layer was washed with brine (5 mL), dried and concentrated. Crude product was purified with silica gel column (0-10 methanol/DCM). Product was obtained and used in next step. (191 mg, 86%); LC/MS: MS (ES+) m/e 202 (MH+).

Workup

  1. customthe Parr shaker (23° C., 50 bar) overnight
  2. customThe catalyst was removed by filtration
  3. customConcentration of filtrate gave desire product
  4. customReaction mixture
  5. concentrationwas concentrated
  6. dissolutiondissolved with ethyl acetate (30 mL) and water (10 mL)
  7. customTwo layers were separated
  8. washOrganic layer was washed with brine (5 mL)
  9. customdried
  10. concentrationconcentrated
  11. customCrude product was purified with silica gel column (0-10 methanol/DCM)
  12. customProduct was obtained

Sources & evidence

ORD record
ord-a534c57498dd4f52b8f3c49b75550fcb
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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