Hydrochloric Acid → 9-Amino-7-chloro-beta-carboline

HRID 1795087Notes

Reaction equation

HRID 1795087 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[N:12]2[N+:15]([O-])=O)=[CH:4][CH:3]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl.Cl>CCO>[NH2:15][N:12]1[C:11]2[CH:10]=[N:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:14][C:2]([Cl:1])=[CH:3][CH:4]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 221852717-Chloro-9-nitro-beta-carbolineHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 221852799-Amino-7-chloro-beta-carbolineYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of the product from example 14 (548 mg, 2.22 mmol) in EtOH (14 ml) at 65° C. to 70° C. was added tin chloride dihydrate (2.5 g, 11.1 mmol). Thereafter, 6M aqueous HCl (14 ml) was added dropwise. The mixture was stirred at 70° C. to 80° C. for 3.5 h and then partitioned slowly into saturated aqueous NaHCO3 (150 ml) and EtOAc (100 ml). The aqueous phase was extracted (2 times) and the combined organic solutions dried (brine; NaSO4) and concentrated to give 484 mg of 9-amino-7-chloro-β-carboline.

Workup

  1. custompartitioned slowly into saturated aqueous NaHCO3 (150 ml) and EtOAc (100 ml)
  2. extractionThe aqueous phase was extracted (2 times)
  3. dry with materialthe combined organic solutions dried (brine; NaSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-060b5160baf24d1381379ab1a4576ab9
Source dataset
uspto-grants-2006_04
Patent number
US07026331B2

Reaction notes

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