Sodium Hydroxide → HCID 19095432, compound

HRID 486586Notes

Reaction equation

HRID 486586 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=13)[N:7]([CH2:15][CH2:16][NH:17][C:18](=O)[CH3:19])[CH:6]=[CH:5]2.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>C(O)C.C(OCC)C>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[CH3:1][C:2]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]2[N:7]3[CH2:15][CH2:16][N:17]=[C:18]([CH3:19])[C:6]3=[CH:5][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 444972Fumaric AcidHCID 19095343HCID 19095343, compound

Product 1

HCID 19095432HCID 19095432, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

N-[2-(5-Methyl-1H-benzo[g]indol-1-yl)ethyl]acetamide (0.3 g) was treated with 3 ml of phosphorous oxychloride under argon and the mixture was heated to 100° C. for 30 minutes. The cooled mixture was added to 250 g of ice-water and treated with 30 ml of 28% sodium hydroxide solution. The mixture was extracted once with 100 ml of methylene chloride and twice with 50 ml of methylene chloride each time, the organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 0.14 g of brown oil, was chromatographed on 10 g of aluminium oxide (neutral, III) with methylene chloride as the eluent. The crude product, 90 mg of yellow-brown, amorphous solid was dissolved in 1 ml of ethanol and 3 ml of diethyl ether and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There were obtained 58 mg (17%) of 10,11-dihydro-5,8-dimethylbenzo[g] pyrazino[1,2-a]indole fumarate (2:1); m.pt.: 184°-186° C. (dec.).

Workup

  1. extractionThe mixture was extracted once with 100 ml of methylene chloride and twice with 50 ml of methylene chloride each time
  2. dry with materialdried with MgSO4
  3. customThe residue, 0.14 g of brown oil, was chromatographed on 10 g of aluminium oxide (neutral, III) with methylene chloride as the eluent
  4. dissolutionThe crude product, 90 mg of yellow-brown, amorphous solid was dissolved in 1 ml of ethanol

Sources & evidence

ORD record
ord-78d7585045904a46be1b57a238fdeee6
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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