4-Chloroaniline → HCID 63623460, compound

HRID 2043330Notes

Reaction equation

HRID 2043330 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[O:9]1[CH2:12][C:11](=O)[CH2:10]1.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:11]2[CH2:12][O:9][CH2:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78124-ChloroanilineHCID 5003444Sodium cyanoborohydrideHCID 150242543-Oxetanone

Product 1

HCID 63623460HCID 63623460, compoundYield 29.4%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

4-Chloroaniline (0.26 g, 2.0 mmol) was dissolved in methanol (25 ml). Then 3-oxetanone (0.22 g, 3 mmol) and zinc chloride (1.09 g, 8.0 mmol) were added and the reaction mixture was cooled with an ice bath. After adding sodium cyanoborohydride (0.377 g, 6.0 mmol) the mixture was allowed to stir at 40° C. for 5 hours. After cooling, the reaction mixture was poured onto ammonium chloride/ice and extracted with ethyl acetate (3 times 20 ml). The organic layer was dried over magnesium sulfate and evaporated. The residue was purified using flash chromatography (heptane/ethyl acetate=95:5) to yield a light yellow liquid (108 mg, 29%); 1H-NMR (CDCl3): 4.14 b, 1H(NH); 4.55 m, 3H(CHO, CHN); 5.00 t, 2H(CHO), 6.43 d, 2H (aryl-H) and 7.15 d, 2H (aryl-H).

Workup

  1. temperaturethe reaction mixture was cooled with an ice bath
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured onto ammonium chloride/ice
  4. extractionextracted with ethyl acetate (3 times 20 ml)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-3a63dcc13fac4f709b2c0c4e3e48393c
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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