2-(Methylamino)ethanol → HCID 12818646, compound

HRID 1703136Notes

Reaction equation

HRID 1703136 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-9d3a0f8cf550468990dd31f21d16321b
Source dataset
uspto-grants-1982_09
Patent number
US04350817

Reaction notes

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