Chloroacetonitrile → HCID 66654475, compound

HRID 2036241Notes

Reaction equation

HRID 2036241 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]1[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[OH:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:30][C:31]#[N:32].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]1[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[O:28][CH2:30][C:31]#[N:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 66653819HCID 66653819, compound

Product 1

HCID 66654475HCID 66654475, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of (±)-1-(5-chloro-2-hydroxy-phenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (1.9 g, 5.00 mmol, 1.00 eq.) and chloroacetonitrile (0.34 mL, 5.19 mmol, 1.04 eq.) in DMSO (1.5 mL) was added to a suspension of potassium carbonate (980 mg, 7.09 mmol, 1.42 eq.) in DMSO (1.5 mL) (exothermic). The mixture was heated up to 80° C. and stirred at that temperature for 1 hour. The reaction mixture was poured onto ice. After the ice melted, the mixture was filtered and the filter cake was rinsed with water. The resulting yellow gum was dried under hv The product was used without further purification.

Workup

  1. additionThe reaction mixture was poured onto ice
  2. filtrationthe mixture was filtered
  3. washthe filter cake was rinsed with water
  4. customThe resulting yellow gum was dried under hv The product
  5. customwas used without further purification

Sources & evidence

ORD record
ord-fb8bcd871c7a45c2a94e476f7665436e
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

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