Sodium Chloride → HCID 18963910, compound

HRID 257062Notes

Reaction equation

HRID 257062 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:20])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CN(C)[CH:28]=[O:29].[NH4+].[Cl-].[Na+].[Cl-]>C1COCC1>[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH:28]([OH:29])[C:17]3[CH:16]=[C:15]([O:18][CH3:19])[CH:14]=[CH:13][C:12]=3[C:11]2=[O:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 1744311HCID 1744311, compoundHCID 178418339Butyllithium

Product 1

HCID 18963910HCID 18963910, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(3-phenylpropyl)-4-methoxybenzamide (5 g, 18.58 mmol) in dry THF (100 ml) is chilled to 5° in an ice/H2O bath. To this, n-butyllithium (1.6 m in hexanes, 59.46 mmol, 37 ml) is added slowly so that the temperature remains below 15°. After the addition is complete, the reaction is stirred for 5 minutes at 5°, followed by the addition of dimethylformamide (4.5 g, 61.31 mmol). After stirring for 1 hour at 10°, saturated NH4Cl solution (10 ml) is added, and the reaction is allowed to warm to room temperature. The reaction is poured into saturated NaCl solution (300 ml) and extracted into EtOAc (300 ml). The EtOAc phase is washed with 2N HCl (300 ml), H2O (300 ml) and saturated NaCl solution (300 ml) dried over MgSO4 and evaporated. The product is purified by chromatography (SiO2 ; 1:9 EtOAc/hexanes, 1:4 EtOAc/hexanes, 2:3 EtOAc/hexanes) yielding 2-(3-phenylpropyl)-5-methoxy-3-hydroxy-1-oxo-1,3-dihydrobenzo[c]pyrrole, as a white solid.

Workup

  1. customremains below 15°
  2. additionAfter the addition
  3. stirringAfter stirring for 1 hour at 10°
  4. extractionextracted into EtOAc (300 ml)
  5. washThe EtOAc phase is washed with 2N HCl (300 ml), H2O (300 ml) and saturated NaCl solution (300 ml)
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe product is purified by chromatography (SiO2 ; 1:9 EtOAc/hexanes, 1:4 EtOAc/hexanes, 2:3 EtOAc/hexanes)

Sources & evidence

ORD record
ord-9b2ebe21ba3547e185dabcfc2c344d14
Source dataset
uspto-grants-1993_11
Patent number
US05260316

Reaction notes

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