Ethanol → HCID 118492331, compound

HRID 710602Notes

Reaction equation

HRID 710602 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[N:9]([O-])=O.[Na+].C(OC(=O)CC([C:21]1[C:22](Cl)=[N:23][CH:24]=[CH:25][CH:26]=1)=C=O)C.[C:29]([O-:32])(=[O:31])[CH3:30].[Na+].[C:34]([O-:37])([O-])=O.[K+].[K+].[CH2:40](O)[CH3:41]>Cl.O.C(Cl)(Cl)Cl>[CH2:40]([O:31][C:29]([C:30]1[C:34](=[O:37])[C:21]2[CH:26]=[CH:25][CH:24]=[N:23][C:22]=2[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[N:9]=1)=[O:32])[CH3:41]

Participants

10

Reactant 6

HCID 702EthanolHCID 11430Potassium CarbonateHCID 115623-BromoanilineHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 118492328HCID 118492328, compound

Product 1

HCID 118492331HCID 118492331, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

In ice-bath, to 3-bromophenylamine (3.87 g, 22.5 mmol) in 20% hydrochloric acid solution (15 mL) was added aqueous NaNO2 (1.66 g, 24 mmol) solution, stirred for 30 min, then added to a mixture solution of 3-(2-chloropyridin-3-yl)-3-carbonylpropionic acid ethyl ester (3.4 g, 15 mmol), sodium acetate (9.85 g, 120.1 mmol) in ethanol (30 mL)/water (30 mL)/chloroform (30 mL), reacted in ice-bath for 15 min, heated to room temperature and reacted for 30 min. After reaction was complete, 30 mL water was added, separated, and organic phase was retained, rotated for dryness. Acetonitrile (50 mL) was added, K2CO3 (2.5 g, 18.1 mmol) was added, heated until refluxing, reacted for 3 h. After reaction was complete, solvent was removed by distillation, crystallization was performed with ethyl ether to obtain product 3.6 g.

Workup

  1. customreacted in ice-bath for 15 min
  2. customreacted for 30 min
  3. customAfter reaction
  4. customseparated
  5. additionAcetonitrile (50 mL) was added
  6. temperatureheated
  7. temperatureuntil refluxing
  8. customreacted for 3 h
  9. customAfter reaction
  10. customsolvent was removed by distillation, crystallization

Sources & evidence

ORD record
ord-7dfb569137f94930be992620ca55eff7
Source dataset
uspto-grants-2015_11
Patent number
US09181244B1

Reaction notes

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