Ammonium Hydroxide → 5,6,7,8-tetrahydroquinoxalin-2-amine

HRID 1464630Notes

Reaction equation

HRID 1464630 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[NH4+:12].[OH-]>[Cu].C(O)(C)C>[NH2:12][C:2]1[CH:11]=[N:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 220369342-Chloro-5,6,7,8-tetrahydroquinoxaline

Product 1

HCID 190871185,6,7,8-tetrahydroquinoxalin-2-amine

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
133 °C

Procedure

A seated tube containing 2-chloro-5,6,7,8-tetrahydroquinoxaline (1.51 g, 0.009 mol), concentrated NH4OH (10 mL), isopropyl alcohol (30 mL), and copper powder (300 mg) was heated in an oil bath at 133° C. for 20 hours. The cooled mixture was filtered through celite and washed through the filter agent with H2O and hexanes. The layers were separated and the aqueous portion was washed (2×) with hexanes in order to remove unreacted starting material and then extracted with EtOAc (4×). The combined EtOAc extracts were dried over sodium sulfate and concentrated under reduced pressure to yield 2-amino-5,6,7,8-tetrahydroquinoxaline as a yellow-green solid.

Workup

  1. filtrationThe cooled mixture was filtered through celite
  2. washwashed through the filter agent with H2O and hexanes
  3. customThe layers were separated
  4. washthe aqueous portion was washed (2×) with hexanes in order
  5. customto remove unreacted
  6. extractionextracted with EtOAc (4×)
  7. dry with materialThe combined EtOAc extracts were dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e0ffffc553747bbbcfafa5ccc4be137
Source dataset
uspto-grants-1994_04
Patent number
US05306819

Reaction notes

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