Phenylhydrazine → HCID 57244202, compound

HRID 2418309Notes

Reaction equation

HRID 2418309 reaction equation
Br[C:2]1(Br)[C:7]2=[N:8][C:9]3[C:14]([C:15](=[O:16])[N:6]2[CH2:5][CH2:4][CH2:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[C:18]1([NH:24][NH2:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(=O)C.[Na+]>C(O)C>[C:18]1([NH:24][N:25]=[C:2]2[C:7]3=[N:8][C:9]4[C:14]([C:15](=[O:16])[N:6]3[CH2:5][CH2:4][CH2:3]2)=[CH:13][CH:12]=[CH:11][CH:10]=4)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 517045Sodium AcetateHCID 125377266,6-Dibromo-6,7,8,9-tetrahydro-11-oxo-11H-pyrido[2,1-b]quinazoline

Product 1

HCID 57244202HCID 57244202, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.8 g. (0.03 mole) 6,6-Dibromo-6,7,8,9-tetrahydro-11-oxo-11H-pyrido[2,1-b]quinazoline and 13.0 g. (0.12 mole] of phenyl hydrazine are heated in 120 ml ethanol for 4 hours. The precipitated crystals are filtered after cooling. When evaporating the mother liquor further crystals are precipitating, which are filtered and washed with some alcohol. The combined filtered product is suspended in 150 ml. of water containing 8.4 g. (0.06 mole) of sodium acetate whereafter it is filtered and washed with water. 8.4 g. (81%) of 6-phenylhydrazono-6,7,8,9-tetrahydro-11-oxo-11H-pyrido[2,1-b]quinazoline are obtained which after recrystallization from isopropanol melts at 177°-179° C. and which does not give a degression of melting point when admixed with the product according to Example 16.

Workup

  1. filtrationThe precipitated crystals are filtered
  2. temperatureafter cooling
  3. customWhen evaporating the mother liquor further crystals
  4. customare precipitating
  5. filtrationwhich are filtered
  6. washwashed with some alcohol
  7. filtrationThe combined filtered product
  8. washwashed with water

Sources & evidence

ORD record
ord-df33ca8a21a7465ab89d0bbbc2685520
Source dataset
uspto-grants-1984_09
Patent number
US04472399

Reaction notes

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