3-Chloroaniline → HCID 178478134, compound

HRID 500527Notes

Reaction equation

HRID 500527 reaction equation
[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=1)[NH2:9].S([NH:23][N:24]=[CH:25][CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(C1C=CC(C)=CC=1)(=O)=O>O.Cl.C(O)C.N1C=CC=CC=1>[Cl:5][C:6]1[CH:7]=[C:8]([N:9]2[N:1]=[C:25]([CH:26]=[CH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:24][NH:23]2)[CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 3

HCID 79323-ChloroanilineHCID 280393Cinnamaldehyde tosyl hydrazoneHCID 23668193Sodium Nitrite

Product 1

HCID 178478134HCID 178478134, compoundYield 19%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

An aqueous (5 mL) solution of sodium nitrite (540.9 mg, 7.839 mmol) was added to a solution of 3-chloroaniline in water (7 mL), concentrated hydrochloric acid (3 mL) and ethanol (7 mL) via dropping funnel. The reaction was allowed to stir at 0° C. for ten minutes. This solution was poured into a dropping funnel and ice was added. This was added dropwise to a solution of the product obtained in example 9.1 (2.3 g, 7.7 mmol) in pyridine (20 mL). This was allowed to stir overnight. An aqueous workup was done extracting with DCM three times. The combined layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (20% EtOAc/hexanes) to yield the title compound as a light purple solid (433 mg, 19%).

Workup

  1. additionThis solution was poured into a dropping funnel
  2. additionice was added
  3. stirringto stir overnight
  4. extractionAn aqueous workup was done extracting with DCM three times
  5. washThe combined layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-01b09495bdd34246aa84085e8139b5a2
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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