2-Chlorobenzaldehyde → HCID 2818274, compound

HRID 483137Notes

Reaction equation

HRID 483137 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=O.[OH-:19].[NH4+]>O>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]1[C:7]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:1][C:8](=[O:19])[NH:9]1

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 8794PhenylacetonitrileHCID 14923Ammonium Hydroxide

Product 1

HCID 2818274HCID 2818274, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

This material was prepared in a similar manner to that described in Acta Chimica Academiae Scientiarum Hungaricae 1969, 60(1-2), 177. Thus a mixture of benzyl cyanide (40 g, 342 mmol) and polyphosphoric acid (200 g) was heated and stirred at 80° C. for 45 minutes. 2-Chlorobenzaldehyde (24 g, 171 mmol) was added with very vigorous stirring over 25 minutes. The mixture was heated to 135° C. for 31/2 h, cooled to 100° C. and poured into water (450 ml). 0.88 Ammonium hydroxide (600 ml) was added and the mixture left overnight. The precipitate was filtered off and refluxed in 5% sodium hydroxide (500 ml). The mixture was filtered hot after 2 h and the solid (30 g) chromatographed (SiO2, 200 g) using chloroform as eluent. This gave a solid that was crystallised (ethanol) to give 1-(2-chlorophenyl)-1,4-dihyroisoquinol-3-one (20.5 g, 47%) m.p. 180°-2° C.

Workup

  1. customThis material was prepared in a similar manner to that
  2. temperaturewas heated
  3. stirringwith very vigorous stirring over 25 minutes
  4. temperatureThe mixture was heated to 135° C. for 31/2 h
  5. temperaturecooled to 100° C.
  6. waitthe mixture left overnight
  7. filtrationThe precipitate was filtered off
  8. temperaturerefluxed in 5% sodium hydroxide (500 ml)
  9. filtrationThe mixture was filtered hot after 2 h
  10. customthe solid (30 g) chromatographed (SiO2, 200 g)
  11. customThis gave a solid
  12. customthat was crystallised (ethanol)

Sources & evidence

ORD record
ord-9742508572d84750804fe68183acd65a
Source dataset
uspto-grants-1986_03
Patent number
US04578393

Reaction notes

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