Dimethylformamide → HCID 20378218, compound

HRID 839696Notes

Reaction equation

HRID 839696 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:22])[CH2:16][C:15]3[C:10](=[C:11]([Cl:20])[C:12]([Cl:19])=[C:13]([O:17][CH3:18])[CH:14]=3)[C:9]2=[O:21])=[CH:4][CH:3]=1.[CH3:23][N:24](C)C=O.[C-]#N.[Na+]>C(Cl)(Cl)Cl>[C:23]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:22])[CH2:16][C:15]3[C:10](=[C:11]([Cl:20])[C:12]([Cl:19])=[C:13]([O:17][CH3:18])[CH:14]=3)[C:9]2=[O:21])=[CH:4][CH:3]=1)#[N:24]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 12423595HCID 12423595, compound

Product 1

HCID 20378218HCID 20378218, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-(4-Bromophenyl)-2-methyl-5-methoxy-6,7-dichloro-1-indanone (8.00 g., 0.02 mole), cuprous cyanide (3.94 g., 0.04 mole) and dimethylformamide (100 ml.) are heated at reflux for 8 hours, added to warm sodium cyanide solution (3 g. in 400 ml. water), extracted with benzene, the benzene solution dried over anhydrous magnesium sulfate, then concentrated in vacuo to give an oily residue. Chromatographing with chloroform on silica gel gives 1.13 g. of 2-(4-cyanophenyl)-2-methyl-5-methoxy-6,7-dichloro-1-indanone melting at 161°-163° C. after crystallization from benzene:hexane, 2:1.

Workup

  1. temperatureat reflux for 8 hours
  2. additionadded
  3. extractionextracted with benzene
  4. dry with materialthe benzene solution dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give an oily residue
  7. customof 2-(4-cyanophenyl)-2-methyl-5-methoxy-6,7-dichloro-1-indanone melting at 161°-163° C. after crystallization from benzene

Sources & evidence

ORD record
ord-6e34272796f745c4a6732472cf3eebb4
Source dataset
uspto-grants-1978_06
Patent number
US04096267

Reaction notes

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