Diisopropylamine → 2-(7-Methoxy-1-naphthyl)-2-oxoacetamide

HRID 1099496Notes

Reaction equation

HRID 1099496 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[C:13](=[O:17])[C:14](O)=[O:15])=[CH:5][CH:4]=1.CCCP(=O)=O.[NH4+].[Cl-].C([NH:29]C(C)C)(C)C>C(#N)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[C:13](=[O:17])[C:14]([NH2:29])=[O:15])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 14462720(7-Methoxy-1-naphthyl)(oxo)acetic acidHCID 16167369Propylphosphoric anhydride

Product 1

HCID 446285742-(7-Methoxy-1-naphthyl)-2-oxoacetamideYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a reactor, 1 g of the compound obtained in Step A is introduced into 30 ml of acetonitrile, and there are then added 4.39 g of propylphosphonic anhydride and 438 mg of NH4Cl and, at the end of the addition, 3.8 ml of diisopropylamine at ambient temperature. The solution is stirred for 4 hours under nitrogen, the solvents are then evaporated off, the residue is taken up in saturated aqueous NaCl solution, and extraction with ethyl acetate is carried out. The solvents are then dried over Na2SO4 and then evaporated off to yield the title product in the form of an orange solid in a yield of 80% and with a chemical purity of 90%.

Workup

  1. customthe solvents are then evaporated off
  2. extractionextraction with ethyl acetate
  3. dry with materialThe solvents are then dried over Na2SO4
  4. customevaporated off

Sources & evidence

ORD record
ord-76d24fd61dce4e10a5841825c1b5b095
Source dataset
uspto-grants-2012_03
Patent number
US08143449B2

Reaction notes

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