Ammonium Hydroxide → 1-amino-5H-pyrido[4,3-b]indole-4-carboxamide

HRID 1896518Notes

Reaction equation

HRID 1896518 reaction equation
Cl[C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[C:5]([C:15]([NH2:17])=[O:16])=[CH:4][N:3]=1.[NH4+:18].[OH-]>>[NH2:18][C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[C:5]([C:15]([NH2:17])=[O:16])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 591984571-chloro-5H-pyrido[4,3-b]indole-4-carboxamide

Product 1

HCID 235819271-amino-5H-pyrido[4,3-b]indole-4-carboxamide

Conditions

Temperature
160 °C

Procedure

A mixture of 1-chloro-5H-pyrido[4,3-b]indole-4-carboxamide in conc. NH4OH (0.07 M) was heated in a microwave reactor at 160° C. for 1 h in a sealed tube. The reaction mixture was cooled to room temperature and partitioned between THF/EtOAc and saturated NaHCO3. After separation of the organic phase, the aqueous phase was extracted again with THF/EtOAc, and the combined organic phases were washed with brine, dried over Na2SO4 and filtered. After evaporation of the organic solvents, the residue was purified by flash chromatography (0-10% MeOH in EtOAc) to provide the title compound as an off-white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between THF/EtOAc and saturated NaHCO3
  3. customAfter separation of the organic phase
  4. extractionthe aqueous phase was extracted again with THF/EtOAc
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customAfter evaporation of the organic solvents
  9. customthe residue was purified by flash chromatography (0-10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-49b2949afb5345aeb15da52b494fad4e
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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