Pyridine → HCID 22407031, compound

HRID 2259276Notes

Reaction equation

HRID 2259276 reaction equation
O.[CH:2]1[C:14]2[CH:13]([CH2:15][CH2:16][C:17]([NH:19][C:20]3[CH:21]=[C:22]([OH:29])[C:23](=[CH:27][CH:28]=3)[C:24]([OH:26])=[O:25])=[O:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C1C2C(C(C)C(O)=O)C3C(=CC=CC=3)C=2C=CC=1.NC1C=C(O)C(=CC=1)C(O)=O.N1C=CC=CC=1.[K+].[Br-]>S(Cl)(Cl)=O.C(Cl)Cl>[CH:11]1[C:12]2[CH:13]([CH2:15][CH2:16][C:17]([NH:19][C:20]3[CH:21]=[C:22]([OH:29])[C:23](=[CH:27][CH:28]=3)[C:24]([OH:26])=[O:25])=[O:18])[C:14]3[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 1049PyridineHCID 46494-Aminosalicylic AcidHCID 253877Potassium BromideHCID 22407011HCID 22407011, compoundHCID 67744427HCID 67744427, compound

Product 1

HCID 22407031HCID 22407031, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Preparation of N-[3-(9-Fluorenyl)propionyl]-4-aminosalicylic acid hydrate was performed as follows. 2-(9-Fluorenyl)propionic acid (1.0 g, 4.2 mmol) was refluxed in 5 ml of thionyl chloride for 1.5 hours and the excess thionyl chloride evaporated in vacuo. The residue was dissolved in 10 ml of methylene chloride and added dropwise to a suspension of 4-aminosalicylic acid (0.64, 4.2 mmol) and pyridine (0.65 ml 8.4 mmol) in 15 ml of methylene chloride. After 3 hours, the reaction was concentrated, taken into ethyl acetate, washed with 10% HCl, and the organic layer dried with magnesium sulfate and concentrated to a tan solid which was purified by reverse phase flash chromatography (C18) eluting with methanol/water 50/50 then 70/30 to give a white solid, mp 225°-228° C. FTIR (KBr) 1643, 1511, 1450, 1367, 1257, 1167, 879, 830, 740, 671 cm-1. 1H NMR (300 MHz, DMSO) δ 1.92 (t, 2H, J=7.5 Hz), 2.35 (m, 2H), 4.09 (t, 1H, J=5.0 Hz), 6.92 (dd, 1H, J=8.5 Hz), 7.24-7.39 (m, 8H), 7.61 (m, 2H), 7.86 (d, 2H, J=7.5 Hz) 9.94 (s, 1H). Anal. calcd for C23H19NO4 0.25H2O: C, 73.09; H, 5.20; N, 3.71. Found: C, 73.19; H, 5.30; N, 3.80.

Workup

  1. customthe excess thionyl chloride evaporated in vacuo
  2. dissolutionThe residue was dissolved in 10 ml of methylene chloride
  3. concentrationthe reaction was concentrated
  4. washwashed with 10% HCl
  5. dry with materialthe organic layer dried with magnesium sulfate
  6. concentrationconcentrated to a tan solid which
  7. customwas purified by reverse phase flash chromatography (C18)
  8. washeluting with methanol/water 50/50
  9. custom70/30 to give a white solid, mp 225°-228° C

Sources & evidence

ORD record
ord-b7e5fe08691d49b5b838f7906dc9e201
Source dataset
uspto-grants-1995_12
Patent number
US05472973

Reaction notes

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