Pyridine → HCID 15295289, compound

HRID 2209725Notes

Reaction equation

HRID 2209725 reaction equation
[C:1]([C:3]1[CH:25]=[CH:24][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[C:16]([OH:23])[CH:15]=2)=[CH:5][CH:4]=1)#[N:2].N1C=CC=CC=1.C(O[C:36](=[O:38])[CH3:37])(=O)C.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[CH:50]([NH:53][CH:54]([CH3:56])[CH3:55])([CH3:52])[CH3:51]>ClCCl>[C:36]([O:23][C:16]1[CH:15]=[C:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:25][CH:24]=2)[CH:22]=[CH:21][C:17]=1[C:18]([N:53]([CH:54]([CH3:56])[CH3:55])[CH:50]([CH3:52])[CH3:51])=[O:20])(=[O:38])[CH3:37]

Participants

8

Reactant 6

HCID 1049PyridineHCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 7918Acetic AnhydrideHCID 65578Oxalyl chlorideHCID 19381507HCID 19381507, compound

Product 1

HCID 15295289HCID 15295289, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4-[5-(4-cyanophenoxy)pentyloxy]-2-hydroxy-benzoic acid (28 g, 82 mmol) in 300 mL of dichloromethane is treated with pyridine (13.3 mL, 164 mmol) and acetic anhydride (9.3 mL, 98.4 retool) and stirred at room temperature for 30 minutes. The reaction is concentrated in vacuo and the residue is partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase is washed with 1N hydrochloric acid and brine, dried over sodium sulfate, and concentrated in vacuo. The resulting 2-acetoxy-4-[5-(4-cyanophenoxy)pentyloxy]-benzoic acid is then dissolved in 300 mL of dichloromethane and treated at 0° C. with oxalyl chloride (8.6 mL, 98.4 mmol) and N,N-dimethylformamide (7.6 mL, 98.4 mmol). This solution is stirred at room temperature for 30 minutes and treated with 30 mL of diisopropylamine at 0° C. After stirring at room temperature for 30 minutes, the reaction is filtered and the filtrate is concentrated in vacuo. The resulting material is partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase is washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford 2-acetoxy-4-[ 5-(4-cyanophenoxy)pentyloxy]-N,N-bis(1-methylethyl)benzamide.

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. customthe residue is partitioned between ethyl acetate and 1N hydrochloric acid
  3. washThe organic phase is washed with 1N hydrochloric acid and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resulting 2-acetoxy-4-[5-(4-cyanophenoxy)pentyloxy]-benzoic acid is then dissolved in 300 mL of dichloromethane
  7. stirringThis solution is stirred at room temperature for 30 minutes
  8. stirringAfter stirring at room temperature for 30 minutes
  9. filtrationthe reaction is filtered
  10. concentrationthe filtrate is concentrated in vacuo
  11. customThe resulting material is partitioned between ethyl acetate and 1N hydrochloric acid
  12. washThe organic phase is washed with brine
  13. dry with materialdried over sodium sulfate
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d4432d9a9454429a982c7b0d8712560
Source dataset
uspto-grants-1995_10
Patent number
US05455274

Reaction notes

Loading…