Sodium Hydroxide → HCID 19095408, compound

HRID 486525Notes

Reaction equation

HRID 486525 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([C:7]2[N:8]([CH2:12][CH2:13][NH:14][C:15](=O)[CH3:16])[CH:9]=[CH:10][CH:11]=2)=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30]>O.C(O)C>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30].[CH3:16][C:15]1[C:9]2[N:8]([C:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:18])=[CH:2][CH:3]=3)=[CH:11][CH:10]=2)[CH2:12][CH2:13][N:14]=1

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 24813Phosphorus oxychlorideHCID 444972Fumaric AcidHCID 19095279HCID 19095279, compound

Product 1

HCID 19095408HCID 19095408, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-[2-(2-p-Tolylpyrrol-1-yl)ethyl]acetamide (3.9 g) was treated with 20 ml of phosphorus oxychloride under argon and boiled for 1/2 hour while stirring. The reaction mixture was hydrolyzed at 0° C. with 100 ml of 2N sodium hydroxide solution and 100 ml of 28% sodium hydroxide solution, diluted with 1000 ml of water and extracted with methylene chloride (1×200 ml, 2×100 ml). The organic extracts were combined, dried with MgSO4 and freed from solvent. 1.7 g of a total of 3.5 g of crude product were dissolved in a 25-fold amount of ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There were obtained 1.8 g (68%) of 3,4-dihydro-1-methyl-6-p-tolylpyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt.: 186°-189° C. (dec.).

Workup

  1. extractionextracted with methylene chloride (1×200 ml, 2×100 ml)
  2. dry with materialdried with MgSO4
  3. dissolution1.7 g of a total of 3.5 g of crude product were dissolved in a 25-fold amount of ethanol

Sources & evidence

ORD record
ord-d48590eaf6ad4c6fa8c7b1194c93d5e4
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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