Pyridine → HCID 19102934, compound

HRID 1198613Notes

Reaction equation

HRID 1198613 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH:13]([CH2:17][CH3:18])[C:14]([OH:16])=[O:15])=[CH:8][CH:7]=[CH:6]2.S(Cl)(Cl)=O.O[N:24]1[C:28](=[O:29])[CH2:27][CH2:26][C:25]1=[O:30].N1C=CC=CC=1>C(Cl)Cl.C1(C)C=CC=CC=1.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH:13]([CH2:17][CH3:18])[C:14]([O:16][CH:26]1[CH2:27][C:28](=[O:29])[NH:24][C:25]1=[O:30])=[O:15])=[CH:8][CH:7]=[CH:6]2

Participants

8

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 80170N-HydroxysuccinimideHCID 19102946HCID 19102946, compound

Product 1

HCID 19102934HCID 19102934, compoundYield 8.3%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(6'methoxynaphthyl)butyric acid (0.519 g, 2.12 mmol) in 20 mL of dry methylene chloride was treated with 3.19 mL of a 2.0 thionyl chloride (6.37 mmol) solution and the resulting solution was allowed to stir overnight. The volatile solvents were removed under vacuum to give the crude acid chloride which was used without further purification. A portion of the acid chloride (139 mg, 0.53 mmol) in 10 mL of dry toluene was added to a stirred solution of N-hydroxysuccinimide (61 mg, 0.53 mmol) and pyridine (42 mg, 0.53 mmol) in 10 mL of dry THF. After stirring overnight, the precipitated pyridine hydrochloride was filtered off and the filtrate concentrated under vacuum. The residue was chromotographed on silica gel (CHCl3 /MeOH) to afford 15 mg of the product as a white solid. Yield 8%; 1H NMR (CDCl3) δ 1.02 (t, 3 H, J=7.4 Hz), 1.95-2.10 (m, 1 H), 2.20-2.35 (m, 1 H), 2.75 (br s, 4 H), 3.91 (m, 4 H), 7.10-7.20 (m, 2 H), 7.40-7.48 (m, 1 H), 7.69-7.82 (m, 3 H); 13C NMR (CDCl3) δ 11.61, 25.34, 26.90, 50.26, 55.23, 105.70, 119.27, 126.31, 127.25, 127.60, 129.04, 129.57, 131.94, 134.23, 158.16, 169.28, 169.78; Anal. Calcd for C19H19NO5 : C, 66.85; H, 5.61; N, 4.10. Found: C, 65.92; H, 5.41; N, 3.64.

Workup

  1. customThe volatile solvents were removed under vacuum
  2. customto give the crude acid chloride which
  3. customwas used without further purification
  4. stirringAfter stirring overnight
  5. filtrationthe precipitated pyridine hydrochloride was filtered off
  6. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-5545024bfec946e5bd73c7a5f5ac17bd
Source dataset
uspto-grants-1994_01
Patent number
US05281617

Reaction notes

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