Acetic Acid → HCID 68217647, compound

HRID 1661055Notes

Reaction equation

HRID 1661055 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7](=O)[CH2:6][CH2:5]2.[C:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:15].CC(O)=O.C([O-])(=O)C.[NH4+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])/[C:7](=[C:16](\[C:14]#[N:15])/[C:17]([O:19][CH2:20][CH3:21])=[O:18])/[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 517165Ammonium AcetateHCID 109214765-Chloro-6-methoxy-1-indanone

Product 1

HCID 68217647HCID 68217647, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To the solution of 5-chloro-6-methoxy-2,3-dihydro-1H-inden-1-one (Prep15, 12 g, 61.2 mmol) in toluene (240 ml) was added ethyl cyanoacetate (8.3 g, 73.46 mmol), AcOH (48 ml, 0.8 mol) and ammonium acetate (12 g, 0.16 mol). The mixture was stirred for 12 hours at 120° C., checked by TLC, concentrated, filtered and washed with water and ethanol twice and purified by FC to afford 11 g of title compound (y=62%).

Workup

  1. concentrationconcentrated
  2. filtrationfiltered
  3. washwashed with water and ethanol twice
  4. custompurified by FC

Sources & evidence

ORD record
ord-6d5a1f520e3e4784be214b4193ac042d
Source dataset
uspto-grants-2011_10
Patent number
US08030322B2

Reaction notes

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