Ethanol → HCID 69021591, compound

HRID 2192232Notes

Reaction equation

HRID 2192232 reaction equation
[CH2:1]([N:8]1[C:20]2[C:19]3[N:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=[C:9]1S(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([OH:27])[CH3:26].[O-]CC.[Na+]>O>[CH2:1]([N:8]1[C:20]2[C:19]3[N:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=[C:9]1[O:27][CH2:25][CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxide2×HCID 69023094HCID 69023094, compound

Product 1

HCID 69021591HCID 69021591, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1-benzyl-2-methanesulfonyl-1H-imidazo[4,5-c][1,5]naphthyridine (6.8 g, 20.1 mmol) was added ethanol (200 mL) and the suspension was stirred at room temperature. To this suspension was added sodium ethoxide (2.0 g) and the reaction was heated at reflux for 1 hour. After 1 hour additional sodium ethoxide was added, and the reaction was heated at reflux for 2 hours and then cooled to ambient. To this reaction was added water (500 mL), and the suspension was stirred for 30 minutes. The gray precipitate was isolated by filtration and washed with water and ether. The solid was dried under reduced pressure to afford 1-benzyl-2-ethoxy-1H-imidazo[4,5-c][1,5]naphthyridine (4.5 g) as a white solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 1 hour
  3. temperaturethe reaction was heated
  4. temperatureat reflux for 2 hours
  5. temperaturecooled to ambient
  6. stirringthe suspension was stirred for 30 minutes
  7. customThe gray precipitate was isolated by filtration
  8. washwashed with water and ether
  9. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-1a1bba36918147d8af4c2b3dc0c2317a
Source dataset
uspto-grants-2012_12
Patent number
US08329721B2

Reaction notes

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