Tetrahydrofuran → 3-Chloro-4-(1-indolinylcarbonylamino)phenylacetic acid

HRID 1372632Notes

Reaction equation

HRID 1372632 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([O:23]CC)=[O:22])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1)=[O:10].[OH-].[Na+].C1COCC1>Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([OH:23])=[O:22])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1)=[O:10]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 17859294Ethyl 3-chloro-4-(1-indolinylcarbonylamino)phenylacetate

Product 1

HCID 178588633-Chloro-4-(1-indolinylcarbonylamino)phenylacetic acidYield 60.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To ethyl 3-chloro-4-(1-indolinylcarbonylamino)phenylacetate (3.07 g, 8.56 mmol) were added 0.25N NaOH (68.4 ml, 17.1 mmol) and THF (70 ml). The mixture was heated and refluxed for 4 hours. After cooling, the reaction mixture was poured in 1N hydrochloric acid (50 ml). The crystals thus precipitated were collected by filtration, and dried under reduced pressure for 12 hours, whereby 3-chloro-4-(1-indolinylcarbonylamino)phenylacetic acid (1.71 g, 60%) was obtained as a colorless crystalline powder.

Workup

  1. temperatureThe mixture was heated
  2. temperaturerefluxed for 4 hours
  3. temperatureAfter cooling
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration
  6. customdried under reduced pressure for 12 hours

Sources & evidence

ORD record
ord-bc9fae70bf514bc6a664cab11690dfa2
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

Loading…