Ethanol → HCID 178507274, compound

HRID 2054371Notes

Reaction equation

HRID 2054371 reaction equation
O=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)[CH2:3][C:4]#[N:5].[NH2:13][NH2:14].CCO.OP(O)(O)=O>O.CO>[Br:12][C:8]1[CH:7]=[C:6]([C:2]2[CH:3]=[C:4]([NH2:5])[NH:13][N:14]=2)[CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 1004Phosphoric Acid2×HCID 9321HydrazineHCID 27568393-(3-Bromophenyl)-3-oxopropanenitrile

Product 1

HCID 178507274HCID 178507274, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

Ten vials were each charged with 3-oxo-3-(3-bromophenyl)propionitrile (1.0 g, 4.5 mmol), hydrazine (0.2 mL) and EtOH (1 mL), and subject to microwave irradiation at 120° C. for 60 min. The contents of all vials was pooled and the solvent was evaporated in vacuo. The crude product was dissolved in ethanol (approx. 200 mL) and acidified by the addition of 4N HLC in dioxane, after 0.5 h the precipitate was collected, washed with additional ethanol and dried to yield 9.60 g. LC/MS (10% MeOH, 90% H2O, 0.2% H3PO4 to 90% MeOH, 10% H2O, 0.2% H3PO4, 2 minute gradient with an Exterra C18 S-5 column 4.6×30 mm): [M+H]+ m/z=239.0, 241.0; retention time=0.85 min.

Workup

  1. customirradiation at 120° C. for 60 min
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe crude product was dissolved in ethanol (approx. 200 mL)
  4. additionacidified by the addition of 4N HLC in dioxane, after 0.5 h the precipitate
  5. customwas collected
  6. washwashed with additional ethanol
  7. customdried
  8. customto yield 9.60 g

Sources & evidence

ORD record
ord-8b32c31192ad435daacb1d57611ee600
Source dataset
uspto-grants-2008_02
Patent number
US07329668B2

Reaction notes

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