Hydrochloric Acid → HCID 17956177, compound

HRID 2103164Notes

Reaction equation

HRID 2103164 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].Cl[CH2:11][CH2:12][C:13](Cl)=[O:14].C([O-])([O-])=O.[K+].[K+].[Al+3].[Cl-].[Cl-].[Cl-].Cl>CC#N>[F:1][C:2]1[CH:3]=[C:4]2[C:6]([CH2:11][CH2:12][C:13](=[O:14])[NH:5]2)=[CH:7][C:8]=1[CH3:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 99573-Fluoro-4-methylanilineHCID 11430Potassium CarbonateHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 17956177HCID 17956177, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
145 °C

Procedure

3-Fluoro-4-methylaniline (1.247 g, 9.96 mmol), 3-chloropropionyl chloride (1.269 g, 9.99 mmol), and K2CO3 (1.450 g, 10.5 mmol) in MeCN (10 mL) were stirred at 40° C. for 3 h. The reaction mixture was quenched with 4M HCl and the product extracted into CH2Cl2. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue (1.168 g) was heated to 145° C. and small portions of AlCl3 (3.538 g, 26.5 mmol) were added over a period of 30 min. The reaction mixture was then cooled and 4M HCl added under stirring followed by extraction of the product into CH2Cl2. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by flash CC (SiO2; CH2Cl2/MeOH 40:1) to give the title compound (97KK40) (0.201 g, total yield 11%). 1H NMR (CDCl3) δ 8.15 (br s, 1H), 6.94 (d, J=7.8 Hz, 1H), 6.47 (d, J=10.0 Hz, 1H), 2.91-2.87 (m, 2H), 2.62-2.60 (m, 2H), 2.19 (d, J=1.8 Hz, CH3).

Workup

  1. customThe reaction mixture was quenched with 4M HCl
  2. extractionthe product extracted into CH2Cl2
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. temperatureThe reaction mixture was then cooled
  7. extractionfollowed by extraction of the product into CH2Cl2
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by flash CC (SiO2; CH2Cl2/MeOH 40:1)

Sources & evidence

ORD record
ord-e19eb96663d248bebb79c6e965b5b7e2
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

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