Water → 2-(7-Methoxy-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 2-methylpropoxyacetate

HRID 1029493Notes

Reaction equation

HRID 1029493 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[CH:21]([OH:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]3=[O:23])=[N:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:31][CH:32]([CH3:39])[CH2:33][O:34][CH2:35][C:36](Cl)=[O:37].O>ClCCCl.CN(C)C1C=CN=CC=1>[CH3:31][CH:32]([CH3:39])[CH2:33][O:34][CH2:35][C:36]([O:23][CH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21](=[O:22])[N:13]1[C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[N:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1)=[O:37]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 14146847Isobutoxyacetyl chlorideHCID 141821812-(7-Methoxy-1,8-naphthyridin-2-yl)-3-hydroxy-1-isoindolinone

Product 1

HCID 700562962-(7-Methoxy-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 2-methylpropoxyacetateYield 62.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution, maintained at a temperature in the region of 20° C., of 2-(7-methoxy-1,8-naphthyridin-2-yl)-3-hydroxy-1-isoindolinone (9.2 g) and triethylamine (20 cc) in 1,2-dichloroethane (150 cc), there is added, in the course of 20 minutes, a solution of 2-methylpropoxyacetyl chloride (9 g) in 1,2-dichloroethane (20 cc) followed by 4-dimethylaminopyridine (50 mg), and the mixture is heated to reflux for 16 hours. The reaction mixture is poured into water (250 cc) and then extracted with methylene chloride (100 cc.) After the extract is washed with water, dried and concentrated to dryness under reduced pressure (3kPa), the residue obtained is purified by two successive recrystallizations in ethanol. 2-(7-Methoxy-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 2-methylpropoxyacetate (7.9 g), m.p. 114° C., is thereby obtained.

Workup

  1. additionis added, in the course of 20 minutes
  2. temperaturethe mixture is heated
  3. temperatureto reflux for 16 hours
  4. extractionextracted with methylene chloride (100 cc.) After the extract
  5. washis washed with water
  6. customdried
  7. concentrationconcentrated to dryness under reduced pressure (3kPa)
  8. customthe residue obtained
  9. customis purified by two successive recrystallizations in ethanol

Sources & evidence

ORD record
ord-4e787b3984744ff483c373a4c8c3e2d9
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

Loading…