Hydrochloric Acid → HCID 18992196, compound

HRID 375621Notes

Reaction equation

HRID 375621 reaction equation
Cl.[Cl:2][C:3]1[CH:10]=[C:9]([Cl:11])[C:6]([CH2:7]Cl)=[C:5]([NH2:12])[CH:4]=1.Cl[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(Cl)(Cl)Cl.CO.Cl>ClC1C=CC=CC=1.C(O)C>[Cl:11][C:9]1[CH:10]=[C:3]([Cl:2])[CH:4]=[C:5]2[C:6]=1[CH2:7][N:15]1[CH:14]=[CH:19][CH:18]=[CH:17][C:16]1=[N:12]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 79772-ChloropyridineHCID 18992527HCID 18992527, compoundHCID 21584188Chloroform methanol

Product 1

HCID 18992196HCID 18992196, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7964ChlorobenzeneSolvent

Procedure

Five grams of the above solid 4,6-dichloro-2-aminobenzyl chloride hydrochloride was heated with 10 mL of 2-chloropyridine in 25 mL of chlorobenzene. The reaction was followed by TLC (300:20:1 chloroform/methanol/28% aqueous ammonia). When the reaction was complete, the reaction mixture was concentrated in vacuo (cold trap). The residue was basified with saturated aqueous potassium carbonate and distributed between 50 mL of chloroform and 50 mL of water. The chloroform layer was separated, dried with anhydrous potassium carbonate and concentrated in vacuo. The brown residue was chromatographed using the above solvent system and the appropriate fractions were concentrated in vacuo to give a yellow solid. This was treated with one equivalent of 4N hydrochloric acid and coevaporated with 50 mL of absolute ethanol. The residue was recrystallized from absolute ethanol-ethyl acetate mixture to give the hydrochloride of 1,3-dichloro-11H-pyrido[2,1-b]quinazoline.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo (cold trap)
  2. customThe chloroform layer was separated
  3. dry with materialdried with anhydrous potassium carbonate
  4. concentrationconcentrated in vacuo
  5. customThe brown residue was chromatographed
  6. concentrationthe appropriate fractions were concentrated in vacuo
  7. customto give a yellow solid
  8. customThe residue was recrystallized from absolute ethanol-ethyl acetate mixture

Sources & evidence

ORD record
ord-bf555f3120ef4860a1d4e457940a4af3
Source dataset
uspto-grants-1996_01
Patent number
US05486512

Reaction notes

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