Hydrochloric Acid → HCID 66781209, compound

HRID 1096749Notes

Reaction equation

HRID 1096749 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@:9]2([C:14]#N)[CH2:11][CH:10]2[CH2:12][OH:13])[CH:5]=[CH:6][C:7]=1[Cl:8].C([OH:18])C.[OH-].[Na+].Cl>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C@:9]23[CH2:11][C@H:10]2[CH2:12][O:13][C:14]3=[O:18])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 59683693HCID 59683693, compound

Product 1

HCID 66781209HCID 66781209, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1S)-1-(3,4-dichloro-phenyl)-2-hydroxymethyl cyclopropanecarbonitrile (10 g, 4.13 mmol), ethanol (20 mL) and 25N sodium hydroxide solution (10 mL) were heated under reflux for 18 hours. The reaction is monitored by TLC (dichloromethane (100%)). The reaction mixture was cooled to room temperature and ice cold water (10 mL) was added to the reaction mass followed by concentrated hydrochloric acid drop wise to adjust the pH of the reaction mass to 1-2 and stirred for overnight at room temperature. The aqueous layer was extracted with dichloromethane (100 mL). The organic layer was washed with 3% sodium bicarbonate solution, dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to yield 4.5 g (45%) of product. 1H NMR δ(300 MHz,CDCl3): 1.41-1.43 (1H,t, J=4.9 Hz), 1.58-1.63 (1H,dd, J=7.79,4.94 Hz), 2.56-2.62 (1H,m), 4.28-4.31 (1H,d, J=9.3 Hz), 4.44-4.48 (1H,dd, J=9.34,4.58 Hz), 7.26-7.30 (1H,dd, J=8.2,2.0 Hz), 7.40-7.43 (1H,d, J=8.2 Hz), 7.52-7.53 (1H,d, J=2 Hz).

Workup

  1. temperatureunder reflux for 18 hours
  2. extractionThe aqueous layer was extracted with dichloromethane (100 mL)
  3. washThe organic layer was washed with 3% sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-01259774a7ba435186607a205051e227
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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