3-chloro-N-phenylpropanamide → Hydrocarbostyril

HRID 1521618Notes

Reaction equation

HRID 1521618 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].Cl[CH2:6][CH2:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9]>CCCCC>[NH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:7][C:8]1=[O:9]

Participants

4

Reactant 2

HCID 2404043-chloro-N-phenylpropanamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 64796Hydrocarbostyril

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of AlCl3 (116.2 g, 0.87 mol) was added 3-chloro-N-phenylpropanamide (74-1; 40 g, 0.22 mol). Reaction mass was heated at 120° C. for 3 h. The reaction mixture was cooled to room temperature and diluted with ice cold water (500 mL) and washed with 1N aqueous hydrochloric acid solution (500 mL) slowly under cooling condition and extracted with ethyl acetate (4×200 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to afford the crude compound which was stirred with n-pentane (250 mL) for 0.5 h and filtered with n-pentane (50 mL) to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 8.33 (bs, 1H), 7.26-7.15 (m, 2H), 7.00-6.97 (t, J=7.4 Hz, 1H), 6.79-6.77 (d, J=7.6 Hz, 1H), 2.99-2.95 (t, J=7.6 Hz, 2H), 2.66-2.63 (t, J=7.4 Hz, 2H). MS (M+1): 148.1.

Workup

  1. customReaction mass
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with 1N aqueous hydrochloric acid solution (500 mL) slowly
  4. temperatureunder cooling condition
  5. extractionextracted with ethyl acetate (4×200 mL)
  6. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under vacuum
  9. customto afford the crude compound which
  10. filtrationfiltered with n-pentane (50 mL)

Sources & evidence

ORD record
ord-867e957f11af465192d62cf450604a8f
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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