Sodium Hydroxide → HCID 178515372, compound

HRID 569031Notes

Reaction equation

HRID 569031 reaction equation
N[C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.N([O-])=[O:16].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O.O>[OH:16][C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 1195373-AminonorharmanHCID 23668193Sodium Nitrite

Product 1

HCID 178515372HCID 178515372, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

0.75 g of 3-amino-β-carboline are dissolved in 85 ml of 6-molar sulfuric acid and at 0° C. mixed with a solution of 0.435 g of sodium nitrite in 10 ml of water. The reaction mixture is stirred for an hour at 0° C. and then added drop by drop to 320 ml of boiling 2-molar sulfuric acid and then refluxed for another 20 minutes. After standing overnight, the product is neutralized with sodium hydroxide and extracted with a mixture consisting of 10 parts of ethyl acetate and one part of ethanol. The ethyl acetate extract is washed once with water, dried and evaporated. The evaporation residue is recrystallized from dimethylformamide. Thus 0.2 g of 3-hydroxy-β-carboline are obtained

Workup

  1. additionadded drop by drop to 320 ml
  2. temperaturerefluxed for another 20 minutes
  3. extractionextracted with a mixture
  4. extractionThe ethyl acetate extract
  5. washis washed once with water
  6. customdried
  7. customevaporated
  8. customThe evaporation residue is recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-5774f51c8f6048468852cfecd5d33832
Source dataset
uspto-grants-1988_03
Patent number
US04731358

Reaction notes

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