Diethylamine → HCID 12818645, compound

HRID 2285828Notes

Reaction equation

HRID 2285828 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[N:8]([CH2:22][CH3:23])[C:9]2[C:14]([C:15]=1[N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=[CH:13][CH:12]=[C:11]([CH3:21])[N:10]=2)=[O:5])[CH3:2].C(NCC)C>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[N:8]([CH2:22][CH3:23])[C:9]2[C:14]([C:15]=1[N:16]([CH2:20][CH3:19])[CH2:17][CH3:18])=[CH:13][CH:12]=[C:11]([CH3:21])[N:10]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 12818639HCID 12818639, compound

Product 1

HCID 12818645HCID 12818645, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.47 g. (0.005 mole) of 1-ethyl-1,2-dihydro-4-chloro-7-methyl-2-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester (Example 30) and 0.7 g. (0.01 mole) of diethylamine in 20 ml. of ethanol was heated in an autoclave placed in a steam bath for 16 hours. The solution was then evaporated in a rotary evaporator and the residue was triturated with 50 ml. of water and was extracted with 50 ml. of diethyl ether. The ether layer was dried over magnesium sulfate, filtered and was evaporated in a rotary evaporator. The residue was recrystallized from heptane. A second recrystallization from petroleum ether gave 0.4 g. of product, m.p. 79°-82° C.

Workup

  1. additionA mixture of 1.47 g
  2. customThe solution was then evaporated in a rotary evaporator
  3. customthe residue was triturated with 50 ml
  4. extractionof water and was extracted with 50 ml
  5. dry with materialThe ether layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customwas evaporated in a rotary evaporator
  8. customThe residue was recrystallized from heptane
  9. customA second recrystallization from petroleum ether
  10. customgave 0.4 g

Sources & evidence

ORD record
ord-b2ddc00d0b5843cea97e639f6c0b6ab4
Source dataset
uspto-grants-1982_04
Patent number
US04324893

Reaction notes

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