Dimethylformamide → HCID 58289913, compound

HRID 2088735Notes

Reaction equation

HRID 2088735 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]([CH3:11])[CH:9]=[O:10].[CH2:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][CH:13]1C(O)=O>C(Cl)(Cl)Cl>[CH3:7][N:8]([CH3:11])[C:9]([CH:18]1[CH2:19][CH2:20][C:21]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:17]1)=[O:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1013701,2,3,4-Tetrahydro-2-naphthoic acid

Product 1

HCID 58289913HCID 58289913, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.94 mL of oxalyl chloride and 0.026 mL of N,N-dimethylformamide were added to a chloroform (20 mL) solution of 3 g of 1,2,3,4-tetrahydronaphthalene-2-carboxylic acid, and stirred at room temperature for 1 hour. The reaction liquid was concentrated, and the residue was dissolved in 20 mL of tetrahydrofuran, and 22.13 mL of 2 M dimethylamine/tetrahydrofuran solution was added thereto. Water was added to the reaction liquid, extracted with ethyl acetate, washed with saturated saline water, dried with anhydrous magnesium sulfate, and the solvent was evaporated away to obtain 3.53 g of the entitled compound as a crude product.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated
  3. dissolutionthe residue was dissolved in 20 mL of tetrahydrofuran
  4. addition22.13 mL of 2 M dimethylamine/tetrahydrofuran solution was added
  5. additionWater was added to the reaction liquid
  6. extractionextracted with ethyl acetate
  7. washwashed with saturated saline water
  8. dry with materialdried with anhydrous magnesium sulfate
  9. customthe solvent was evaporated away

Sources & evidence

ORD record
ord-5f3aa1c95acd43f3a20b80b1e5d25a45
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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