Sodium Hydroxide → HCID 19095347, compound

HRID 486522Notes

Reaction equation

HRID 486522 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]([CH2:14][CH2:15][NH:16][C:17](=O)[CH3:18])[CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31]>O.C(O)C>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]3[CH2:14][CH2:15][N:16]=[C:17]([CH3:18])[C:11]3=[CH:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 24813Phosphorus oxychlorideHCID 444972Fumaric AcidHCID 19095285HCID 19095285, compound

Product 1

HCID 19095347HCID 19095347, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-[2-[2-(3,4-Dichlorophenyl)-pyrrol-1-yl]ethyl]-acetamide (4.6 g) was treated with 25 ml of phosphorus oxychloride under argon and boiled for 1 hour while stirring. The reaction mixture was hydrolyzed at 0° C. with 70 ml of 2N sodium hydroxide solution and 120 ml of 28% sodium hydroxide solution, diluted with 1400 ml of water and extracted with methylene chloride (1×500 ml, 2×250 ml). The organic extracts were combined, dried with MgSO4 and freed from solvent. 2.0 g of a total of 3.8 g of crude product were dissolved in a 20-fold amount of ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There were obtained 2.1 g (65%) of 6-(3,4-dichlorophenyl)-3,4-dihydro-1-methylpyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt.: 193°-195° C. (dec.).

Workup

  1. extractionextracted with methylene chloride (1×500 ml, 2×250 ml)
  2. dry with materialdried with MgSO4
  3. dissolution2.0 g of a total of 3.8 g of crude product were dissolved in a 20-fold amount of ethanol

Sources & evidence

ORD record
ord-34df39a36dbc493b878008e4d93f64bf
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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