Acetonitrile → 2-Cyano-5-(3-phenoxypropoxy)indan-1,3-dione

HRID 2057601Notes

Reaction equation

HRID 2057601 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:22]([O:24]C)=O)[C:15](=[CH:20][CH:21]=1)[C:16]([O:18]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26](#[N:28])[CH3:27].[H-].[Na+]>CCOCC>[C:26]([CH:27]1[C:22](=[O:24])[C:14]2[C:15](=[CH:20][CH:21]=[C:12]([O:11][CH2:10][CH2:9][CH2:8][O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:13]=2)[C:16]1=[O:18])#[N:28]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 20331397Dimethyl 4-(3-phenoxypropoxy)phthalate

Product 1

HCID 203314172-Cyano-5-(3-phenoxypropoxy)indan-1,3-dioneYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of dimethyl 4-(3-phenoxypropoxy)phthalate (6.5 g; 0.019 mole), acetonitrile (10 ml) and sodium hydride (0.69 g of 100%) was stirred at 100° for 6 hours and dry ether added to the cooled yellow product. The solid which separated was filtered off, dissolved in water and the solution strongly acidified with concentrated hydrochloric acid. Filtration of the precipitated solid gave the title compound which recrystallised from ethanol dilute hydrochloric acid with mp 148°-150° (dec) and in 86% yield. (Found; C, 69.00; H, 4.90; N, 4.41; C19H15NO4 0.5H2O requires; C, 69.08; H, 4.88; N, 4.24%).

Workup

  1. customThe solid which separated
  2. filtrationwas filtered off
  3. dissolutiondissolved in water
  4. filtrationFiltration of the precipitated solid

Sources & evidence

ORD record
ord-fb4e6091c4b54142b9ee859af17a7837
Source dataset
uspto-grants-1980_07
Patent number
US04211791

Reaction notes

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