Morpholine → HCID 12818641, compound

HRID 2285829Notes

Reaction equation

HRID 2285829 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].N1CC[O:28]CC1.C(=O)([O-])[O-].[Na+].[Na+]>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]1[CH2:17][CH2:18][O:28][CH2:19][CH2:20]1)=[CH:13][CH:12]=[C:11]([CH3:21])[N:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10340Sodium CarbonateHCID 12818639HCID 12818639, compound

Product 1

HCID 12818641HCID 12818641, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 0.59 g. (0.002 mole) of 1-ethyl-1,2-dihydro-4-chloro-7-methyl-2-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester (Example 30), 0.17 g. (0.002 mole) of morpholine and 0.2 g. (0.002 mole) of sodium carbonate in 20 ml. of ethanol was heated under reflux for 4 hours. The mixture was filtered and the filtrate was diluted with water to the cloudy point. The precipitate which formed was collected, air dried and was recrystallized from heptane to afford 0.2 g. of product, m.p. 129°-131° C.

Workup

  1. additionA stirred mixture of 0.59 g
  2. temperatureunder reflux for 4 hours
  3. filtrationThe mixture was filtered
  4. additionthe filtrate was diluted with water to the cloudy point
  5. customThe precipitate which formed
  6. customwas collected
  7. customair dried
  8. customwas recrystallized from heptane
  9. customto afford 0.2 g

Sources & evidence

ORD record
ord-24e78bc0e51e41c49af663c86addb136
Source dataset
uspto-grants-1982_04
Patent number
US04324893

Reaction notes

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