Sodium Hydroxide → 4-(3-(2-(7-Bromoquinolin-2-yl)ethynyl)-phenoxy)butanoic acid sodium salt

HRID 1088465Notes

Reaction equation

HRID 1088465 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:26]=[CH:27][CH:28]=3)[O:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+:30]>C1COCC1.CCO>[Na+:30].[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]#[C:13][C:14]3[CH:15]=[C:16]([CH:26]=[CH:27][CH:28]=3)[O:17][CH2:18][CH2:19][CH2:20][C:21]([O-:23])=[O:22])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53654124Ethyl 4-(3-(2-(7-bromoquinolin-2-yl)ethenyl)phenoxy)butyrate

Product 1

HCID 703593594-(3-(2-(7-Bromoquinolin-2-yl)ethynyl)-phenoxy)butanoic acid sodium salt

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ethyl ester from Step 4 (380 mg) in THF (4 mL) and EtOH (2 mL) was added 2N NaOH (0.65 mL) and the mixture was stirred overnight at room temperature. The reaction mixture was evaporated to dryness and passed through a neutral XAD-8 resin, eluting with H2O and then with EtOH, to afford the title compound as a white solid: m.p. 250° C. (d).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. washeluting with H2O

Sources & evidence

ORD record
ord-0e1c0af7de7843e1bd66f72f2e42dcc9
Source dataset
uspto-grants-1990_10
Patent number
US04962203

Reaction notes

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