Hydrochloric Acid → HCID 67350745, compound

HRID 1670728Notes

Reaction equation

HRID 1670728 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]([CH3:16])([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[N:2].Cl>[Pd].CO>[NH2:2][CH2:1][C:3]1[N:8]=[CH:7][C:6]([CH:9]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:10]([CH3:16])([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67349699HCID 67349699, compound

Product 1

HCID 67350745HCID 67350745, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 3-(6-cyanopyridin-3-yl)-2,2-dimethyl-3-phenylpropanoate (0.24 g, 0.81 mmol), palladium (10% on carbon, 93 mg), concentrated hydrochloric acid (0.19 mL), and methanol (7 mL) was stirred under hydrogen (balloon) for 2.5 hr. The mixture was then filtered. The filtrate was concentrated to remove methanol. The residue was made basic with saturated aqueous sodium bicarbonate solution (10 mL) and extracted with ethyl acetate (4×10 mL). The combined ethyl acetate extracts were washed with brine (5 mL), dried (Na2SO4) and concentrated to give methyl 3-(6-(aminomethyl)pyridin-3-yl)-2,2-dimethyl-3-phenylpropanoate (0.24 g, 0.80 mmol, 99% yield) as a solid. MS found: (M+H)+=299.31.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationThe filtrate was concentrated
  3. customto remove methanol
  4. extractionextracted with ethyl acetate (4×10 mL)
  5. washThe combined ethyl acetate extracts were washed with brine (5 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a158922f2c634dbca6536bcba28d72c8
Source dataset
uspto-grants-2011_08
Patent number
US07994190B2

Reaction notes

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