HCID 19867644, compound → HCID 19867665, compound

HRID 1199052Notes

Reaction equation

HRID 1199052 reaction equation
[CH3:1][O:2][C:3]1[N:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([N:13]3[C:21](=O)[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]3[O:23][CH2:24][C:25]([OH:27])=[O:26])=[N:10]2)=[CH:5][CH:4]=1.COC1N=C2C(C=CC(N3CC4C(=CC=CC=4)C3OCC(OC(C)(C)C)=O)=N2)=CC=1>FC(F)(F)C(O)=O.C(OC(C)C)(C)C>[CH3:1][O:2][C:3]1[N:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([N:13]3[CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]3[O:23][CH2:24][C:25]([OH:27])=[O:26])=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 19867644HCID 19867644, compoundHCID 54405395HCID 54405395, compound

Product 1

HCID 19867665HCID 19867665, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7914Diisopropyl EtherSolvent

Procedure

[2-(7-Methoxy-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyloxy]acetic acid may be prepared in the following manner: a solution of tert-butyl [2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinyloxy]acetate (29.4 g) in trifluoroacetic acid is stirred for 2 hours at a temperature in the region of 25° C. The reaction mixture is then concentrated to dryness and the residue obtained is stirred in isopropyl ether (200 cc). The crystallized solid obtained is separated by filtration and then taken up with water (400 cc). The mixture is brought to pH 10 with 4N aqueous sodium hydroxide solution. An insoluble product is separated by filtration; the filtrate is washed with ethyl acetate (3×200 cc) and then acidified to pH 2 with 4N aqueous hydrochloric acid solution. The precipitate obtained is separated by filtration, washed with water and dried in the air. [2-(7-Methoxy-1,8-naph-thyridin-2-yl)-1-isoindolinyloxy]acetic acid (14.6 g), m.p. 190° C., is thereby obtained.

Workup

  1. concentrationThe reaction mixture is then concentrated to dryness
  2. customthe residue obtained
  3. customThe crystallized solid obtained
  4. customis separated by filtration
  5. customAn insoluble product is separated by filtration
  6. washthe filtrate is washed with ethyl acetate (3×200 cc)
  7. customThe precipitate obtained
  8. customis separated by filtration
  9. washwashed with water
  10. customdried in the air

Sources & evidence

ORD record
ord-67d414282f3440ad8e515d2d337d4b9b
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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