Oxalyl chloride → HCID 68810203, compound

HRID 2217898Notes

Reaction equation

HRID 2217898 reaction equation
[C:1](Cl)(=O)[C:2](Cl)=O.[Cl:7][C:8]1[CH:17]=[CH:16][C:15]2[N:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]=1[C:18]([OH:20])=O>ClCCl.CN(C)C=O>[Cl:7][C:8]1[CH:17]=[CH:16][C:15]2[N:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]=1[C:18]([NH:14][CH2:13][CH2:12][CH:2]1[CH2:1][CH2:10][CH2:9][CH2:8][CH2:17]1)=[O:20]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 57721343HCID 57721343, compound

Product 1

HCID 68810203HCID 68810203, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.3 mL) was added to a suspension of 6-chloro-5-quinolinecarboxylic acid (example 94(a)) (0.3 g) in dichloromethane and 2 drops of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 1 hour then evaporated to an oil. The residue was added to cyclohexylethylamine hydrochloride (0.33 g) and triethylamine (0.6 mL) in dichloromethane and then stirred at room temperature for 1 hour. Water was added and the reaction mixture was extracted with dichloromethane. The combined organics were dried and concentrated. Purification (SiO2, ethyl acetate:isohexane 50:50) gave the sub titled compound as a solid (0.115 g).

Workup

  1. customthen evaporated to an oil
  2. additionThe residue was added to cyclohexylethylamine hydrochloride (0.33 g) and triethylamine (0.6 mL) in dichloromethane
  3. stirringstirred at room temperature for 1 hour
  4. additionWater was added
  5. extractionthe reaction mixture was extracted with dichloromethane
  6. customThe combined organics were dried
  7. concentrationconcentrated
  8. customPurification (SiO2, ethyl acetate:isohexane 50:50)

Sources & evidence

ORD record
ord-9b69bd1a8bbb49e2a29f3a9c4fc5b535
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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