Sulfuric acid magnesium salt (1:1) → HCID 178519067, compound

HRID 1467736Notes

Reaction equation

HRID 1467736 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH2:16][O:17][C:18]2=[O:23].S([O-])([O-])(=O)=O.[Mg+2]>C(#N)C>[N:1]1[C:10]2[C:5](=[CH:6][C:7](/[CH:11]=[N:13]/[C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[CH2:16][O:17][C:18]4=[O:23])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 7656536-QuinolinecarbaldehydeHCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-one

Product 1

HCID 178519067HCID 178519067, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of quinoline-6-carbaldehyde (786 mg, 5.0 mmol), 4-aminoisobenzofuran-1(3H)-one (745 mg, 5.0 mmol) and anhydrous magnesium sulfate (6.0 g, 50.0 mmol) in acetonitrile (100 ml) was heated at reflux for two days. The solution was filtered and removed in vacuum. The crude product was re-crystallized from isopropanol to give the title compound (1.348 g, yield 93%) LC-MS (ESI) m/z: 289 (M+1)+. 1H-NMR (400 MHz, DMSO-d) δ (ppm): 5.57 (s, 2H), 7.63-7.77 (m, 4H), 8.14-8.16 (d, J=8.8 Hz, 1H), 8.39-8.42 (m, 1H), 8.53-8.56 (m, 2H), 8.99-9.01 (m, 2H).

Workup

  1. temperatureat reflux for two days
  2. filtrationThe solution was filtered
  3. customremoved in vacuum
  4. customThe crude product was re-crystallized from isopropanol

Sources & evidence

ORD record
ord-629f4d3fca2a4ebe9468909337f4ff0f
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

Loading…