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Water → HCID 67313673, compound

HRID 2190388
Notes
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Reaction equation

HRID 2190388 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][C:20]=2[F:28])[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].[Cl-].[Ca+2].[Cl-].O>C(O)C>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][C:14]2[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:29]=[CH:30][CH:31]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=3)[CH:17]=[CH:16][CH:15]=2)=[C:20]([F:28])[CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 67312595HCID 67312595, compound

Product 1

HCID 67313673HCID 67313673, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 3-(1-cyano-1-methylethyl)-N-[3-(2-fluoro-4-nitrophenoxy)phenyl]benzamide (2.03 g, 4.83 mmol), calcium chloride (1.41 g, 12.1 mmol) and reduced iron (2.97 g, 53.1 mmol) in ethanol (300 mL)/water (30 mL) was stirred with heating at 80° C. for 12 hr. The reaction mixture was cooled to room temperature, and passed through a pad filled with celite to separate insoluble material, and the insoluble materials were washed with ethanol. The filtrate and washing were combined and concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (300 mL), washed with 5% aqueous sodium hydrogencarbonate solution (300 mL), water (200 mL×2) and saturated brine (200 mL), successively, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30→0/100), and the obtained solution was concentrated under reduced pressure to give the title compound (1.94 g, quantitatively) as a yellow amorphous substance.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionfilled with celite
  3. customto separate insoluble material
  4. washthe insoluble materials were washed with ethanol
  5. washThe filtrate and washing
  6. concentrationconcentrated under reduced pressure
  7. additionThe obtained residue was diluted with ethyl acetate (300 mL)
  8. washwashed with 5% aqueous sodium hydrogencarbonate solution (300 mL), water (200 mL×2) and saturated brine (200 mL)
  9. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  10. filtrationThe insoluble material was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30→0/100)
  13. concentrationthe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8b52eb9b137a4587b06a4bfc23fb845c
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08324395B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes