Quinoline → HCID 21422773, compound

HRID 259060Notes

Reaction equation

HRID 259060 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=1)[NH:12][C:13](=[O:18])[CH2:14][C:15](=[O:17])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22]([O-])([O-])[O:23]C.N1C2C(=CC=CC=2)C=C[CH:28]=1>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=1)[NH:12][C:13](=[O:18])[CH2:14][C:15]([O:23][CH3:22])([O:17][CH3:28])[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7047QuinolineHCID 21422799m-Benzyloxy-acetylacetanilideHCID 53629101Methylorthoformate

Product 1

HCID 21422773HCID 21422773, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 70 g of m-benzyloxy-acetylacetanilide, 37 g of methyl orthoformate and 100 ml of methanol was stirred at 20°C. for 16 hours and 2 ml of quinoline were added thereto. The mixture was concentrated to dryness under reduced pressure and the residue was added to isopropyl ether. The mixture was cooled and vacuum filtered and the recovered precipitate was dried and chromatographed over silica gel. Elution with an 8-2 methylene chloride-acetone mixture gave 48 g of m-benzyloxy-3,3-dimethoxy-butyranilide melting at 83°C.

Workup

  1. concentrationThe mixture was concentrated to dryness under reduced pressure
  2. additionthe residue was added to isopropyl ether
  3. temperatureThe mixture was cooled
  4. filtrationvacuum filtered
  5. customthe recovered precipitate was dried
  6. customchromatographed over silica gel
  7. washElution with an 8-2 methylene chloride-acetone mixture

Sources & evidence

ORD record
ord-e899e55cffdd4097b6cc3643bfaf8c46
Source dataset
uspto-grants-1977_07
Patent number
US04036633

Reaction notes

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