Hydrogen Bromide → HCID 15271015, compound

HRID 2205223Notes

Reaction equation

HRID 2205223 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[C:4]([CH3:9])[C:3]=1[CH3:10].[CH2:11](OC(OCC)CBr)[CH3:12].Br>C(O)(C)C.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([CH3:9])[C:5]2[N:6]([CH:11]=[CH:12][N:8]=2)[N:7]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 69919433-Amino-6-chloro-4,5-dimethylpyridazine

Product 1

HCID 15271015HCID 15271015, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 6-chloro-4,5-dimethylpyridazin-3-amine (2.00 g, 12.7 mmol, 1.0 equiv) in isopropanol (40 mL) was added bromoacetaldehyde diethyl acetal (5.23 mL, 34.8 mmol, 2.7 equiv), and hydrobromic acid (2.00 mL) and heated to reflux for 2 h. The reaction mixture was diluted with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. Purification by column chromatography using 20% ethyl acetate in hexanes elution gave 2.07 g of the white solid, 90%.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. extractionextracted with ethyl acetate
  4. customPurification by column chromatography
  5. wash20% ethyl acetate in hexanes elution

Sources & evidence

ORD record
ord-28d4f76faee947cdaf49df60bb75dbb4
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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