Pyridine → HCID 59204417, compound

HRID 2242587Notes

Reaction equation

HRID 2242587 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH3:19])([CH3:18])[CH:16]=O)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:20]1C=CC=[CH:22][CH:21]=1.C([O-])(=O)C.[NH4+].C(CC(O)=O)#N>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH3:19])([CH3:18])/[CH:16]=[CH:22]/[C:21]#[N:20])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 9740Cyanoacetic acidHCID 517165Ammonium AcetateHCID 198553592-(3-(Benzyloxy)phenyl)-2-methylpropanal

Product 1

HCID 59204417HCID 59204417, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyloxy aldehyde III (320 g, 1.26 mol) in toluene (1.2 L) was added pyridine (600 mL), ammonium acetate (15 g, 0.19 mol) and cyanoacetic acid (200 g, 2.35 mol) and the mixture was refluxed for 72 hours. The reaction was diluted with ethyl acetate (3.5 L), washed with water (2 L) and washed with 1N HCl (until pH of the water layer becomes acidic), washed with brine (1 L) and the organic layer was dried and concentrated under reduced pressure to yield 317 g (91 %) cyanide XXXIV. M+1=278

Workup

  1. temperaturethe mixture was refluxed for 72 hours
  2. washwashed with water (2 L)
  3. washwashed with 1N HCl (until pH of the water layer
  4. washwashed with brine (1 L)
  5. customthe organic layer was dried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1aa5d3cdc839457f9d4a3ae708732422
Source dataset
uspto-grants-2010_03
Patent number
US07671052B2

Reaction notes

Loading…