Acetyl chloride → HCID 19865415, compound

HRID 414735Notes

Reaction equation

HRID 414735 reaction equation
[OH-].[OH:2][C:3]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5](=[O:19])[C:4]=1[NH+:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.C(N(CC)CC)C.[C:32](Cl)(=[O:34])[CH3:33].[OH-].[K+]>C(Cl)Cl.O>[C:32]([O:2][C:3]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5](=[O:19])[C:4]=1[N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)(=[O:34])[CH3:33]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 54680203HCID 54680203, compound

Product 1

HCID 19865415HCID 19865415, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(1,2-dihydro-4-hydroxy-1-phenyl-2-oxo-1,8-naphthyridin-3-yl)-pyrrolidinium hydroxide, inner salt (3 g) and triethylamine (1.41 g) in CH2Cl2 (50 mL) was stirred at room temperature in an atmosphere of nitrogen. Acetyl chloride (1.09 g) was added dropwise and stirring was continued for a total of about 20-24 hours. The product was poured into water (200 mL) and the pH was adjusted to 7 with 10% KOH solution. The organic layer was separated and dried (Na2SO4). The dry solution was filtered and evaporated to a solid which was recrystallized from isopropanol to yield the desired product, 2.17 g (67%) m.p. 197°-200° C.

Workup

  1. stirringstirring
  2. customwas continued for a total of about 20-24 hours
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationThe dry solution was filtered
  6. customevaporated to a solid which
  7. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-728f75f63ff14ebfacd21e835e98b4f8
Source dataset
uspto-grants-1988_12
Patent number
US04794116

Reaction notes

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