4-Chlorobenzaldehyde → HCID 21847944, compound

HRID 618732Notes

Reaction equation

HRID 618732 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:22].[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.[NH4+:32].[OH-]>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:22]=[C:28]([C:27]3[CH:30]=[CH:31][C:24]([Cl:23])=[CH:25][CH:26]=3)[NH:32][C:9]=2[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 21847939HCID 21847939, compound

Product 1

HCID 21847944HCID 21847944, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 100 mg (0.345 mmol) of 1-(4-bromophenyl)-2-(4-pyridyl)-ethan-1,2-dione (from Step B), 266 mg (3.45 mmol) of ammonium acetate, and 61 mg (0.0.431 mmol) of 4-chlorobenzaldehyde in 2 mL of acetic acid was heated at 90° C. for 3 h. The green reaction mixture was treated with excess 2:1 NH4OH/sat. NH4Cl and extracted with ethyl acetate and chloroform 3 times. The organic layers were combined and washed with water, brine, and dried over sodium sulfate. After removal of solvents, the residue was flash chloromatographed over silica gel (gradient elution, 1-4% MeOH in DCM) to give 75 mg of the titled compound, homogeneous by TLC (9:1 DCM/MeOH); mass spectrum (CI) m/e 411, 413 (M+1)+.

Workup

  1. extractionNH4Cl and extracted with ethyl acetate and chloroform 3 times
  2. washwashed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvents

Sources & evidence

ORD record
ord-af3e0d688d4047a9adb4430b1d02ed4a
Source dataset
uspto-grants-1999_09
Patent number
US05955480

Reaction notes

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