Hydrochloric Acid → HCID 86718835, compound

HRID 1024333Notes

Reaction equation

HRID 1024333 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:17])[C:11]#[C:12][Si:13]([CH3:16])([CH3:15])[CH3:14])([O-])=O.Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:17])[CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86718834HCID 86718834, compound

Product 1

HCID 86718835HCID 86718835, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 1-(2-nitrophenyl)-3-(trimethylsilyl)prop-2-yn-1-one (11) (294 g; 1.19 mole) in toluene (4.5 L) was added Pd/C (10% wt; 30 g) under N2. The resulting suspension was degassed under vacuum and back-filled 3-times with H2. The mixture was hydrogenated under 0.3 MPa of hydrogen at room temperature for 72 hours. The progress of the reaction was monitored by HPLC. When the HPLC analysis indicated the disappearance of compound (II), the catalyst was filtered off through a Celite pad. The filtrate was concentrated under vacuum to give the crude product as black liquid. HPLC analysis showed 90% purity. The crude product was dissolved in ethyl acetate (7.5 L) and treated with 4N hydrochloric acid (600 mL). After the phase separation, HPLC analysis showed the 92.8% purity. The organic phase was washed again with 4 N hydrochloric acid (600 mL). The organic phase was further washed with 4 N hydrochloric acid (500 mL) one additional time. The organic phase was dried over sodium sulfate (200 g), concentrated to give the crude product (3) (220 g; 84% yield).

Workup

  1. customThe resulting suspension was degassed under vacuum
  2. additionback-filled 3-times with H2
  3. filtrationthe catalyst was filtered off through a Celite pad
  4. concentrationThe filtrate was concentrated under vacuum
  5. customto give the crude product as black liquid
  6. customAfter the phase separation, HPLC analysis
  7. washThe organic phase was washed again with 4 N hydrochloric acid (600 mL)
  8. washThe organic phase was further washed with 4 N hydrochloric acid (500 mL) one additional time
  9. dry with materialThe organic phase was dried over sodium sulfate (200 g)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c67e93112a98405d903399cd2cf4647c
Source dataset
uspto-grants-2014_05
Patent number
US08722886B1

Reaction notes

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