Acetic Acid → HCID 68217607, compound

HRID 1661048Notes

Reaction equation

HRID 1661048 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH2:6][CH2:5]2.[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:13].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[C:14](\[C:12]#[N:13])/[C:15]([O:17][CH2:18][CH3:19])=[O:16])/[CH2:6][CH2:5]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 1425995-Chloro-1-indanoneHCID 517165Ammonium Acetate

Product 1

HCID 68217607HCID 68217607, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 5-chloro-2,3-dihydro-1H-inden-1-one (150 g, 0.9 mol, commercially available) and ethyl cyanoacetate (125 g, 1.1 mol), ammonium acetate (150 g, 1.94 mmol) and glacial acetic acid (500 mL) in benzene (1 L) was refluxed with a Dean Stark water trap for 22 h. Then benzene was partially removed under vacuum, the residue was filtered and the solid obtain was crystallized from ethanol to give the title compound (161 g, y=68%).

Workup

  1. customThen benzene was partially removed under vacuum
  2. filtrationthe residue was filtered
  3. customthe solid obtain
  4. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-49d9513bb7224537a7564dc6b7ac3519
Source dataset
uspto-grants-2011_10
Patent number
US08030322B2

Reaction notes

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