2-(Methylamino)ethanol → HCID 12818646, compound

HRID 2285830Notes

Reaction equation

HRID 2285830 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]C[CH2:18][CH2:17]1)=[CH:13][CH:12]=[C:11]([CH3:21])[N:10]=2)=[O:5])[CH3:2].CNCC[OH:29].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]([CH2:17][CH2:18][OH:29])[CH3:20])=[CH:13][CH:12]=[C:11]([CH3:21])[N:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 10340Sodium CarbonateHCID 12818639HCID 12818639, compound

Product 1

HCID 12818646HCID 12818646, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred 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), 0.38 g. (0.005 mole) of 2-methylaminoethanol and 0.53 g. (0.005 mole) of sodium carbonate in 20 ml. of ethanol was heated under reflux for 5 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 ethyl acetate to afford 0.5 g. of product, m.p. 111°-113° C.

Workup

  1. additionA stirred mixture of 1.47 g
  2. temperatureunder reflux for 5 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 ethyl acetate
  9. customto afford 0.5 g

Sources & evidence

ORD record
ord-4060bb4a091847428e4b1339e2b5ed8d
Source dataset
uspto-grants-1982_04
Patent number
US04324893

Reaction notes

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