4-Chlorobenzaldehyde → HCID 20242664, compound

HRID 483138Notes

Reaction equation

HRID 483138 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[OH-:21].[NH4+]>[OH-].[Na+]>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]2[C:4]3[C:5](=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:9][C:10](=[O:21])[NH:11]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 14923Ammonium HydroxideHCID 88310(3-Methoxyphenyl)acetonitrile

Product 1

HCID 20242664HCID 20242664, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3-methoxyphenylacetonitrile (25 g) and polyphosphoric acid (110 g) was heated and stirred at 90°-110° C. for 45 mins. 4-Chlorobenzaldehyde (12 g) was added in portions over 25 mins., with vigorous stirring. The mixture was heated at 120°-130° C. for 3 h, cooled and poured into a mixture of 0.88 ammonium hydroxide (2.5 liters) and 10% sodium hydroxide (200 ml), and left overnight. The precipitate was filtered off, washed with water, dissolved in chloroform (150 ml) and chromatographed on silica gel (500 g) using 1:1 ethyl acetate-pentane as the eluent. Recovery of the first band to be eluted, followed by recrystallisation from chloroform-pentane, afforded 1-(4-chlorophenyl)-8-methoxy-1,4-dihydroisoquinol-3-one (DESCRIPTION 17), 1.2 g, m.p. 250°-251° C.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was heated at 120°-130° C. for 3 h
  3. temperaturecooled
  4. waitleft overnight
  5. filtrationThe precipitate was filtered off
  6. washwashed with water
  7. dissolutiondissolved in chloroform (150 ml)
  8. customchromatographed on silica gel (500 g)
  9. washRecovery of the first band to be eluted
  10. customfollowed by recrystallisation from chloroform-pentane

Sources & evidence

ORD record
ord-022587f107334bf1bad6d14592739992
Source dataset
uspto-grants-1986_03
Patent number
US04578393

Reaction notes

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