Acetyl chloride → HCID 58368355, compound

HRID 1851098Notes

Reaction equation

HRID 1851098 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[F:5][C:6]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:7]=1[O:8][C:9]1[C:10]2[N:11]([CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:13][CH:14]=1.[C:25](Cl)(=[O:27])[CH3:26].C(=O)(O)[O-].[Na+]>ClC(Cl)C>[F:5][C:6]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:7]=1[O:8][C:9]1[C:10]2[N:11]([CH:15]=[CH:16][C:17]=2[C:25](=[O:27])[CH3:26])[N:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 587990064-(2-Fluoro-4-nitrophenoxy)pyrrolo[1,2-b]pyridazine

Product 1

HCID 58368355HCID 58368355, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

AlCl3 (1.46 g, 10.98 mmol) was added to a solution of 4-(2-fluoro-4-nitrophenoxy)pyrrolo[1,2-b]pyridazine (600 mg, 2.19 mmol) in dichloroethane (60 mL). After stirring at room temperature for 1 hour and adding acetyl chloride (0.17 mL, 2.42 mmol), the mixture was further stirred for 3 hours. The resulting reaction mixture was neutralized with saturated sodium bicarbonate aqueous solution. The resulting mixture was filtered through celite. After phase separation of the filtrate, the organic layer was dried with magnesium sulfate and then filtered. The filtrate was concentrated and then purified by silica gel chromatography (1-6% ethyl acetate in dichloromethane) to give the target compound as a white solid (640 mg, 2.03 mmol, 93% yield).

Workup

  1. stirringthe mixture was further stirred for 3 hours
  2. customThe resulting reaction mixture
  3. filtrationThe resulting mixture was filtered through celite
  4. customAfter phase separation of the filtrate
  5. dry with materialthe organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. custompurified by silica gel chromatography (1-6% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-29d0495e48954bd9b9a381956d7e888a
Source dataset
uspto-grants-2015_02
Patent number
US08957102B2

Reaction notes

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