Water → HCID 10586886, compound

HRID 841187Notes

Reaction equation

HRID 841187 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[Cu][C:20]#[N:21].O.C(OCC)(=O)C>CN(C=O)C.C1(C)C=CC=CC=1>[C:20]([C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])#[N:21]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 347783(3-Chloro-4-nitrophenyl)(phenyl)methanoneHCID 178418546HCID 178418546, compound

Product 1

HCID 10586886HCID 10586886, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
67.5 °C

Procedure

A stirred mixture of 3-chloro-4-nitrobenzophenone (5.00 g), (J. Org. Chem., 1962, 27, 1605-1608), and copper(I)cyanide (2.57 g) in DMF (50 ml) was heated at reflux for 16 hours. The hot reaction mixture was then poured into a stirred solution of ferric chloride (15.30 g) concentrated hydrochloric acid (5 ml) and water (200 ml). The mixture was heated at 65-70° C. for 30 minutes, cooled to ambient temperature treated with ethyl acetate (250 ml) and stirred vigorously for 5 minutes. The organic phase was separated and the aqueous layer extracted with another 250 ml portion of ethyl acetate. The combined organics were dried, filtered and evaporated to give a brown oil. Chromatography (eluent toluene) gave the title compound (2.77 g) as a yellow solid. M.p. 117-119° C.; EA C14H8N2O3 requires C, 66.67; H, 3.02; N, 11.11%; found: C, 66.83; H, 2.99; N, 11.12%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. temperaturecooled to ambient temperature
  4. customThe organic phase was separated
  5. extractionthe aqueous layer extracted with another 250 ml portion of ethyl acetate
  6. customThe combined organics were dried
  7. filtrationfiltered
  8. customevaporated
  9. customto give a brown oil

Sources & evidence

ORD record
ord-e1e8303fdc714f33b8368fbb91695c6b
Source dataset
uspto-grants-2002_04
Patent number
US06369273B1

Reaction notes

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