Hydrochloric Acid → HCID 21584389, compound

HRID 583287Notes

Reaction equation

HRID 583287 reaction equation
[CH2:1]1[CH:13]2[N:4]([CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH2:12]2)[CH2:3][CH2:2]1.[N+:14]([O-])([O-:16])=[O:15].[K+].[OH-].[NH4+].[ClH:21]>S(=O)(=O)(O)O.C(O)(C)C.C(O)C>[ClH:21].[N+:14]([C:8]1[CH:9]=[CH:10][C:11]2[CH2:12][CH:13]3[CH2:1][CH2:2][CH2:3][N:4]3[CH2:5][C:6]=2[CH:7]=1)([O-:16])=[O:15]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 13150100HCID 13150100, compound

Product 1

HCID 21584389HCID 21584389, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1118Sulfuric AcidSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of 1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinoline (4.12 g, 23.8 mmol) in concentrated sulfuric acid (100 ml) at -10° C. was added, in portions over 1 h, potassium nitrate (2.40 g, 23.7 mmol). After addition was complete, the reaction mixture was stirred for 1 h before it was poured over ice. The aqueous solution was made basic with concentrated ammonium hydroxide and the product was extracted into dichloromethane (twice). The dried (magnesium sulfate) organic phase was concentrated to give a red oil that solidified on standing. This solid was taken up in isopropanol (100 ml) and hydrogen chloride in ethanol was added until acidic. The solid was collected, washed with isopropanol and dried to give the crude product (3.39 g, 56%). This solid was recrystallized from ethanol to give the title compound (2.16 g, 36%) as an off-white solid, m.p. 231-3° C. (dec.).

Workup

  1. additionAfter addition
  2. additionwas poured over ice
  3. extractionthe product was extracted into dichloromethane (twice)
  4. dry with materialThe dried (magnesium sulfate) organic phase
  5. concentrationwas concentrated
  6. customto give a red oil that
  7. customThe solid was collected
  8. washwashed with isopropanol
  9. customdried
  10. customto give the crude product (3.39 g, 56%)
  11. customThis solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-4c7a9b76cbc64758a7813b682bde73a4
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

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