Water → HCID 14621100, compound

HRID 1607198Notes

Reaction equation

HRID 1607198 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([Cl:11])[C:3]=1Br.O.CCOC(C)=O.C(Cl)Cl.[CH3:23][N:24](C=O)C>>[C:8]([C:5]1[C:4]([Cl:11])=[C:3]([C:23]#[N:24])[C:2]([NH2:1])=[CH:7][CH:6]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 14621088HCID 14621088, compoundHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 14621100HCID 14621100, compound

Procedure

A mixture of 4'-amino-3'-bromo-2'-chloroacetophenone (17 g, 58 mmol) and cuprous cyanide (5.2 g, 58 mmol) is warmed in DMF (85 mL) to 80°-100° C. for 6 hours, then poured into H2O (1.5 L), stirred for 15 minutes and filtered. The brown solid was washed with H2O (200 mL) and then boiled in EtOAc (500 mL) and filtered. This extraction is repeated. The EtOAc filtrate is washed twice with 20% NH4Cl (500 ml), twice with H2O (500 mL), dried with Na2SO4, and evaporated to give a brown solid. After flash column chromatography (SiO2, EtOAc-CH2Cl2, 1:20), the product is isolated as a yellow solid; yld. 5.5 g (48%); m.p. 189°-193° C.

Workup

  1. filtrationfiltered
  2. washThe brown solid was washed with H2O (200 mL)
  3. filtrationfiltered
  4. extractionThis extraction
  5. washThe EtOAc filtrate is washed twice with 20% NH4Cl (500 ml), twice with H2O (500 mL)
  6. dry with materialdried with Na2SO4
  7. customevaporated
  8. customto give a brown solid

Sources & evidence

ORD record
ord-cb4cd9acb5b94e31876a56b0547a575f
Source dataset
uspto-grants-1989_09
Patent number
US04863959

Reaction notes

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