Ammonium Chloride → HCID 19068900, compound

HRID 1957128Notes

Reaction equation

HRID 1957128 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][C:13]1[C:22]([O:23][CH3:24])=[N:21][C:20]2[C:15](=[CH:16][C:17]([CH3:30])=[C:18]([CH3:29])[C:19]=2[C:25](OC)=[O:26])[N:14]=1.[Cl-].[NH4+]>ClCCl>[CH3:11][O:12][C:13]1[C:22]([O:23][CH3:24])=[N:21][C:20]2[C:15](=[CH:16][C:17]([CH3:30])=[C:18]([CH3:29])[C:19]=2[CH2:25][OH:26])[N:14]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 19068876HCID 19068876, compoundHCID 21225700Diisobutylaluminumhydride2×

Product 1

HCID 19068900HCID 19068900, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisobutylaluminium hydride (19.9 mL, 1M in dichloromethane, 19.9 mmol) was added dropwise over 30 minutes to a stirred solution of 2,3-dimethoxy-6,7-dimethyl-5-(methoxycarbonyl)quinoxaline (5.0 g, 18.1 mmol) in dry dichloromethane (300 mL) under nitrogen at -90° C. After 1 hour, another portion of diisobutylaluminium hydride (19.9 mL) was added, and the mixture was stirred for a further 1.5 hours. Saturated aqueous ammonium chloride (100 mL) was added, and the mixture was allow to warm to room temperature. The mixture was filtered through Arbocel filter aid, and the filtrate was washed thoroughly with dichloromethane. The aqueous layer was separated and extracted with two portions of dichloromethane. The combined organic solutions were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography to give 2,3-dimethoxy-6,7-dimethyl-5-hydroxymethyl quinoxaline (1.25 g, 28%).

Workup

  1. filtrationThe mixture was filtered through Arbocel
  2. filtrationfilter aid
  3. washthe filtrate was washed thoroughly with dichloromethane
  4. customThe aqueous layer was separated
  5. extractionextracted with two portions of dichloromethane
  6. dry with materialThe combined organic solutions were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c8e0eb4bd78542428c8c92f978321368
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

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