Sodium Hydroxide → HCID 68585671, compound

HRID 18460Notes

Reaction equation

HRID 18460 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:3]=1.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:3]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 680234-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58685855HCID 58685855, compound

Product 1

HCID 68585671HCID 68585671, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-amino-2-(2-methoxy-ethoxymethoxy)-benzonitrile (666 mg; 3 mmol) in 1,2-dichloroethan (15 mL) was added 4-fluorobenzaldehyd (496 mmol; 4 mmol) and carefully sodium triacetoxyborohydride (933 mg; 4.4 mmol). The mixture was stirred at 60° C. for 6 hours. The reaction mixture was added 1 M NaOH (aq.), dried by filtering through a silicone filter, evaporated onto SiO2 and purified by column chromatography (SiO2-heptane/EtOAc=2:1) to yield 700 mg pure product.

Workup

  1. customdried
  2. filtrationby filtering through a silicone
  3. filtrationfilter
  4. customevaporated onto SiO2
  5. custompurified by column chromatography (SiO2-heptane/EtOAc=2:1)

Sources & evidence

ORD record
ord-a23d0548a5034b45a08ddc1e183be5e0
Source dataset
uspto-grants-2010_06
Patent number
US07741352B2

Reaction notes

Loading…