HCID 20137333, compound → HCID 14456192, compound

HRID 1253222Notes

Reaction equation

HRID 1253222 reaction equation
[CH2:1]([O:3][C:4]([C:6]1(C([O-])=O)[CH:18]([CH2:19][O:20][CH3:21])[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:22][O:23][CH2:24][CH3:25])[NH:10][C:9]=2[CH2:8][NH:7]1)=[O:5])[CH3:2]>C1(C)C(C)=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([CH2:22][O:23][CH2:24][CH3:25])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 20137333HCID 20137333, compound

Product 1

HCID 14456192HCID 14456192, compoundYield 7.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1,2,3,4-Tetrahydro-3-ethoxycarbonyl-5-ethoxymethyl-4-methoxymethyl-β-carboline-3-carboxylate (6.8 g) in xylene (1.11) is boiled under reflux for 1 hour. The xylene is evaporated in vacuo and the residue is dissolved in methylene chloride (600 ml). 2,3-Dichloro-5,6-dicyano-p-benzoquinone (4.5 g) is added in one portion to the ice-cooled solution. After 5 minutes stirring the solution is washed with 1.2 vol. % of aqueous ammonia, and the methylene chloride is removed by destillation in vacuo. The residue, after two chromatographies on silicagel, first with a mixture of methylene chloride and acetone (1:1), and then with a mixture of methylene chloride and methanol (95:5) yields 0.46 g of pure 5-ethoxymethyl-4-methoxymethyl-β-carboline-3-carboxylic acid ethylester. M.p. 94°-97° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe xylene is evaporated in vacuo
  3. dissolutionthe residue is dissolved in methylene chloride (600 ml)
  4. addition2,3-Dichloro-5,6-dicyano-p-benzoquinone (4.5 g) is added in one portion to the ice-
  5. temperaturecooled solution
  6. washis washed with 1.2 vol. % of aqueous ammonia
  7. customthe methylene chloride is removed by destillation in vacuo
  8. additionThe residue, after two chromatographies on silicagel, first with a mixture of methylene chloride and acetone (1:1)
  9. additionwith a mixture of methylene chloride and methanol (95:5)

Sources & evidence

ORD record
ord-6d2876500e624a38a4ce1d725545d2e2
Source dataset
uspto-grants-1988_05
Patent number
US04748180

Reaction notes

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