4-Chlorobenzaldehyde → HCID 178519073, compound

HRID 1968044Notes

Reaction equation

HRID 1968044 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Mg+2].[NH2:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH2:19][O:20][C:21]2=[O:26]>C(#N)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[N:16]/[C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[CH2:19][O:20][C:21]3=[O:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-one

Product 1

HCID 178519073HCID 178519073, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 4-chlorobenzaldehyde (2.3 g, 16.1 mmol) and anhydrous magnesium sulfate (16 g, 134 mmol) in anhydrous acetonitrile (200 ml) was added 4-aminoisobenzofuran-1(3H)-one (2 g, 13.4 mmol) at room temperature. After the addition, the mixture was stirred at reflux for overnight. The mixture was filtered and the cake was washed with ethyl acetate (50 mL×3). The filtrate was concentrated to give crude product. The crude product was washed with petroleum ether and re-crystallized from ethyl acetate to give the title compound (2 g, yield: 55%). LC-MS (ESI) m/z: 272 (M+1)+.

Workup

  1. additionAfter the addition
  2. temperatureat reflux for overnight
  3. filtrationThe mixture was filtered
  4. washthe cake was washed with ethyl acetate (50 mL×3)
  5. concentrationThe filtrate was concentrated
  6. customto give crude product
  7. washThe crude product was washed with petroleum ether
  8. customre-crystallized from ethyl acetate

Sources & evidence

ORD record
ord-1a7f18624fef42ca97857d6139d8277b
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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