2-Naphthalenesulfonic acid → HCID 19691978, compound

HRID 1632

Reaction equation

HRID 1632 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][CH2:6]2.C(O[C:14]1[O:15][CH2:16][CH2:17][N:18]=1)C.C1C2C(=CC=CC=2)C=CC=1S(O)(=O)=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([C:14]1[O:15][CH2:16][CH2:17][N:18]=1)[CH2:6]2

Participants

5

Reactant 3

HCID 84202-Naphthalenesulfonic acidHCID 127306402-Ethoxy-4,5-dihydro-1,3-oxazoleHCID 147958674-Fluoro-2,3-dihydro-1H-isoindole

Product 1

HCID 19691978HCID 19691978, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluoroisoindoline (400 mg), 2-ethoxy-2-oxazoline (400 mg), and β-naphthylsulfonic acid (30 mg) in 50 ml of toluene was stirred at 100° C. for 1 hour. The solvent as removed under reduced pressure, and the residue chromatographed on silica gel, eluting with 1-4% methanol in ethyl acetate, to give 4-fluoro-2-(oxazolin-2-yl)isoindoline, a compound of Formula (IB), m.p. 125°-129° C.

Workup

  1. customThe solvent as removed under reduced pressure
  2. customthe residue chromatographed on silica gel
  3. washeluting with 1-4% methanol in ethyl acetate

Sources & evidence

ORD record
ord-0aed4da618f94372b6ebcb5dce352131
Source dataset
uspto-grants-1998_03
Patent number
US05726197

Linked notes

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