Water → 2-acryloylamino-5-[pyridazin-3(2H)-on-6-yl]indane

HRID 1077427Notes

Reaction equation

HRID 1077427 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[NH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:16]3[CH:17]=[CH:18][C:19](=[O:22])[NH:20][N:21]=3)[CH:13]=2)[CH2:8]1.Br.O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[C:1]([NH:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:16]3[CH:17]=[CH:18][C:19](=[O:22])[NH:20][N:21]=3)[CH:13]=2)[CH2:8]1)(=[O:4])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13140Acryloyl chlorideHCID 189297722-amino-5-[pyridazin-3(2H)-on-6-yl]indane hydrobromide

Product 1

HCID 199728542-acryloylamino-5-[pyridazin-3(2H)-on-6-yl]indaneYield 80.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under ice cooling, 3.0 g of acryloyl chloride dissolved in 50 ml of tetrahydrofuran was added dropwise to a suspension of 5.03 g of 2-amino-5-[pyridazin-3(2H)-on-6-yl]indane·hydrobromide in 150 ml of ethyl acetate and 150 ml of water containing 4.52 g of potassium carbonate, and the mixture was stirred for 3 hours. Crystals precipitated were collected by filtration, washed with water, dried and then recrystallized from methanol-acetonitrile to obtain 3.69 g of 2-acryloylamino-5-[pyridazin-3(2H)-on-6-yl]indane.

Workup

  1. customCrystals precipitated
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. customdried
  5. customrecrystallized from methanol-acetonitrile

Sources & evidence

ORD record
ord-99af5a186c2e40ba956f8123a329b311
Source dataset
uspto-grants-1996_08
Patent number
US05543409

Reaction notes

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