Hydrochloric Acid → HCID 21449345, compound

HRID 597064

Reaction equation

HRID 597064 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([N:13]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[N:14]=CC)=[N:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.Cl>C(O)C>[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([N:13]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[NH2:14])=[N:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86734555acetaldehyde N1-(7-chloroquinazolin-4-yl)p-methoxyphenylhydrazone hydrochloride

Product 1

HCID 21449345HCID 21449345, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of acetaldehyde N1 -(7-chloroquinazolin-4-yl)-p-methoxyphenylhydrazone hydrochloride (15.0g.) in ethanol (120ml.; dried over magnesium ethoxide) was cooled and stirred at 5°-10° C for 3 hrs. during the passage of dry hydrogen chloride. The mixture was then left at 0°-5° C. for 3 days before separation by filtration. The solid was washed with dry ether (10ml.), and then dissolved in a mixture of water (30ml.), saturated sodium acetate solution (5ml.) and ethyl acetate (25ml.). The aqueous layer was extracted with more ethyl acetate (2 × 15ml.), and the extracts washed with water (20ml.), dried (Na2SO4) and evaporated to give N1 -(7-chloroquinazolin-4-yl)-p-methoxyphenylhydrazine, m.p. 124°-127° C.

Workup

  1. temperaturewas cooled
  2. waitThe mixture was then left at 0°-5° C. for 3 days before separation by filtration
  3. washThe solid was washed with dry ether (10ml.)
  4. dissolutiondissolved in a mixture of water (30ml.), saturated sodium acetate solution (5ml.) and ethyl acetate (25ml.)
  5. extractionThe aqueous layer was extracted with more ethyl acetate (2 × 15ml.)
  6. washthe extracts washed with water (20ml.)
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-5bc2e9d69aee48f691891766db751553
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Linked notes

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