Sodium Hydroxide → HCID 19095337, compound

HRID 486575Notes

Reaction equation

HRID 486575 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][N:4]([CH2:7][CH2:8][NH:9][C:10](=O)[CH3:11])[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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(OCC)(=O)C>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30].[CH3:11][C:10]1[C:5]2[N:4]([C:3]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:2]([CH3:1])[CH:6]=2)[CH2:7][CH2:8][N:9]=1

Participants

8

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 24813Phosphorus oxychlorideHCID 444972Fumaric AcidHCID 19095305HCID 19095305, compound

Product 1

HCID 19095337HCID 19095337, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[2-[3-Methyl-2-phenylpyrrol-1-yl]ethyl]acetamide (2.6 g) was treated with 20 ml of phosphorus oxychloride under argon and boiled under reflux for 1 hour. 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 (1×300 ml, 2×150 ml). The organic extracts were combined, washed once with 100 ml of water, dried with MgSO4 and freed from solvent. 2.1 g of crude product were dissolved in a 25-fold amount of ethanol at the boiling temperature and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. After the addition of 50 ml of ethyl acetate 2.0 g of pale yellow crystals separated and were recrystallized from ethyl acetate/ethanol (1:1). There were obtained 1.3 g (30%) of 3,4-dihydro-1,7-dimethyl-6-phenylpyrrolo[1,2-a]pyrazine fumarate (2:3); m.pt.: 157°-159° C. (dec.).

Workup

  1. temperatureunder reflux for 1 hour
  2. extractionextracted with methylene chloride (1×300 ml, 2×150 ml)
  3. washwashed once with 100 ml of water
  4. dry with materialdried with MgSO4
  5. dissolution2.1 g of crude product were dissolved in a 25-fold amount of ethanol at the boiling temperature
  6. customseparated
  7. customwere recrystallized from ethyl acetate/ethanol (1:1)

Sources & evidence

ORD record
ord-46bd655faffe4ac0899aed2c47bd3d97
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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