Hydrazine → HCID 178469916, compound

HRID 1466641Notes

Reaction equation

HRID 1466641 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH:21]2[CH2:23][CH2:22]2)=[C:6]([CH:19]=1)[C:7]([C:9](=[CH:15][N:16](C)C)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=O.[NH2:24]N>CC(O)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH:21]2[CH2:23][CH2:22]2)=[C:6]([C:7]2[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:15][NH:16][N:24]=2)[CH:19]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 66846726HCID 66846726, compound

Product 1

HCID 178469916HCID 178469916, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-(5-chloro-2-cyclopropoxybenzoyl)-3-(dimethyl-amino)acrylate (24 g, 71 mmol) was dissolved in 150 mL of HOAc. The reaction mixture was cooled to 0° C. then 85% hydrazine in water (25 mL) was added dropwise. The mixture was warmed to room temperature and stirred for 6 hours, then concentrated in vacuo. The residue was purified by EtOAc/Hexanes=1:2 to afford 24 g of the title compound as a syrup. 1H NMR (DMSO-d6, 400 MHz) δ: 13.41 (s, 1H), 8.26 (s, 0.5H), 7.88 (s, 0.5H), 7.49-7.24 (m, 3H), 4.07-3.99 (m, 2H), 3.82-3.74 (m, 1H), 1.17-1.10 (m, 3H), 0.73-0.46 (m, 4H).

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by EtOAc/Hexanes=1:2

Sources & evidence

ORD record
ord-6633c275a55e42009f3a1c959d888bce
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

Loading…