4-Cyanobenzoic acid → HCID 68592844, compound

HRID 1516616Notes

Reaction equation

HRID 1516616 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:2].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.[ClH:17].O1CCOCC1>C(O)C>[ClH:17].[NH:2]=[C:1]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 120874-Cyanobenzoic acidHCID 31268PyrrolidineHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 68592844HCID 68592844, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
35 °C

Procedure

4-Cyanobenzoic acid (10.0 g, 68.0 mmol) was dissolved in anhydrous ethanol (10 ml) and 4N hydrochloric acid/1,4-dioxane 90 ml, and the mixture was stirred in a closed system at room temperature for two nights, and further stirred in an open system for at 35° C. 3 hours. The solvent was evaporated under reduced pressure, and the obtained residue was suspended in anhydrous ethanol (100 ml), and pyrrolidine (11.4 ml, 136 mmol) was added thereto, and the mixture was stirred at room temperature overnight. The precipitated crystals were collected by filtration, and washed with diethyl ether containing a small amount of 4N hydrochloric acid/1,4-dioxane, and the crystals were collected by filtration to give the title compound.

Workup

  1. custom3 hours
  2. customThe solvent was evaporated under reduced pressure
  3. stirringthe mixture was stirred at room temperature overnight
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with diethyl ether containing a small amount of 4N hydrochloric acid/1,4-dioxane
  6. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-3f010af10f6245128ebbcfe4bef4e007
Source dataset
uspto-grants-2012_07
Patent number
US08227506B2

Reaction notes

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