Sulfuric Acid → HCID 20308038, compound

HRID 1287289Notes

Reaction equation

HRID 1287289 reaction equation
[CH2:1]1[CH:14]2[CH:5]([C:6]3[C:11]([CH2:12][CH2:13]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4][CH2:3][CH:2]1C(O)=O.OS(O)(=O)=O.[N-:23]=[N+]=[N-].[Na+]>C(Cl)(Cl)Cl>[NH2:23][CH:2]1[CH2:3][CH2:4][CH:5]2[CH:14]([CH2:13][CH2:12][C:11]3[C:6]2=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:1]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 20308055HCID 20308055, compound

Product 1

HCID 20308038HCID 20308038, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 11.7 g (0.05 mole) of 1,2,3,4,4a,9,10,-10a-octahydrophenanthrene-2-carboxylic acid, 80 ml of conc. H2SO4 and 200 ml of CHCl3 is added with stirring at 50°-60° 3.64 g of sodium azide in small portions. After completed addition, heating at 50° is continued for 1 hr longer, the the mixture poured onto ice and then rendered alkaline with caustic. The product is extracted into CHCl3, dried and freed of solvent to give about 9 g of 2-amino-1,2,3,4,4a,-9,10,10a-octahydrophenanthrene, which is subjected to a Birch reduction as per Example 1E and then reacted with hydrogen peroxide in the presence of formic acid as per Example 1F to form the title compound.

Workup

  1. additionis added
  2. additionaddition
  3. temperatureheating at 50°
  4. additionlonger, the the mixture poured onto ice
  5. extractionThe product is extracted into CHCl3
  6. customdried

Sources & evidence

ORD record
ord-2103a679b6514eea8a4007e2df976b0e
Source dataset
uspto-grants-1976_10
Patent number
US03984419

Reaction notes

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