Ammonium Chloride → HCID 10499233, compound

HRID 1957133Notes

Reaction equation

HRID 1957133 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[C:13]([CH2:27][N:28]2[CH:32]=[C:31]([C:33](OC)=[O:34])[N:30]=[N:29]2)=[C:14]2[C:19](=[CH:20][C:21]=1[Cl:22])[N:18]=[C:17]([O:23][CH3:24])[C:16]([O:25][CH3:26])=[N:15]2.[Cl-].[NH4+]>CO>[Cl:11][C:12]1[C:13]([CH2:27][N:28]2[CH:32]=[C:31]([CH:33]=[O:34])[N:30]=[N:29]2)=[C:14]2[C:19](=[CH:20][C:21]=1[Cl:22])[N:18]=[C:17]([O:23][CH3:24])[C:16]([O:25][CH3:26])=[N:15]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10501028HCID 10501028, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 10499233HCID 10499233, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of diisobutylaluminium hydride (1M in dichloromethane, 9 mL, 9 mmol) was added dropwise to a stirred suspension of 6,7-dichloro-2,3-dimethoxy-5-[(4-methoxycarbonyl-1,2,3-triazol-1-yl)methyl]quinoxaline (1.087 g, 2.73 mmol) under nitrogen at -78° C. After 2.25 hours, methanol (5 mL) was added, followed by saturated aqueous ammonium chloride (25 mL) 5 minutes later. The mixture was allowed to warm to room temperature, filtered through Arbocel filter aid, washing the filter cake with dichloromethane. The organic solution was dried (MgSO4) and concentrated under reduced pressure to give 6,7-dichloro-2,3-dimethoxy-5[(4-formyl-1,2,3-triazol-1-yl)methyl]quinoxaline (981 mg, 98%), as a white solid.

Workup

  1. filtrationfiltered through Arbocel
  2. filtrationfilter aid
  3. washwashing the filter cake with dichloromethane
  4. dry with materialThe organic solution was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cc94e8c48ca0485cbaff9b86c2775b46
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

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