5-Chlorovaleryl chloride → HCID 86749801, compound

HRID 1378445Notes

Reaction equation

HRID 1378445 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH3:19])=[C:9]2[C:20]([O:22][CH3:23])=[O:21])[CH:5]=[CH:6][CH:7]=1.[Cl:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30]>C1COCC1>[Cl:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:9]([C:20]([O:22][CH3:23])=[O:21])=[C:10]([CH3:19])[NH:11][C:12]([CH3:18])=[C:13]2[C:14]([O:16][CH3:17])=[O:15])[CH:5]=[CH:6][CH:7]=1)=[O:30]

Participants

4

Reactant 2

HCID 740895-Chlorovaleryl chlorideHCID 11645365HCID 11645365, compound

Product 1

HCID 86749801HCID 86749801, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

4-(3-Aminophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylic acid, dimethyl ester (2.3 g, 7.28 mmol) was dissolved in THF (50 mL) and cooled to 0° C. 5-Chlorovaleryl chloride (1.13 g, 7.28 mmol) was dissolved in THF (15 mL) and added dropwise to the mixture over 15 min. The mixture was stirred at 0° C. for 1 h., the solvent removed in vacuo, and the residue was extracted using CH2Cl2 /water. The CH2Cl2 layer was dried over Na2SO4, filtered, and concentrated in vacuo. Silica gel chromatography (1:1 to 1:0 EtOAc:hexane gradient) of the concentrate gave the title compound (3.16 g, 100%) as a pale yellow foam.

Workup

  1. additionadded dropwise to the mixture over 15 min
  2. customthe solvent removed in vacuo
  3. extractionthe residue was extracted
  4. dry with materialThe CH2Cl2 layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6375e9d22f82409aa41d05f0bfa3e4d0
Source dataset
uspto-grants-1997_09
Patent number
US05668151

Reaction notes

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