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

HRID 1168725Notes

Reaction equation

HRID 1168725 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-eb0ed0f057214944bb6f3f7c7d231355
Source dataset
uspto-grants-2003_09
Patent number
US06627637B2

Reaction notes

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