4-Fluorobenzylamine → HCID 6483031, compound

HRID 897378Notes

Reaction equation

HRID 897378 reaction equation
[OH:1][C:2]1[C:3]([C:12]([O:14]C)=O)=[N:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1>CO>[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH:22][C:12]([C:3]2[C:2]([OH:1])=[C:11]3[C:6]([CH:7]=[CH:8][CH:9]=[N:10]3)=[CH:5][N:4]=2)=[O:14])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 22346294Methyl 8-hydroxy-1,6-naphthyridine-7-carboxylate

Product 1

HCID 6483031HCID 6483031, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 8-hydroxy-1,6-naphthyridine-7-carboxylate (10.0 grams, 48.9 mmol) prepared as described in Example 1 was dissolved/suspended in MeOH (100 mL) and treated with 4-fluorobenzylamine (6.1 g, 48.9 mmol). The reaction was brought to reflux and the MeOH allowed to evaporate until the total volume was approximately 30 mL. The reaction was refluxed for 5 hours more and a white solid precipitated. The reaction was cooled and the solid collected by filtration, washed with a minimum of MeOH and dried on the pump to give the product as a white solid.

Workup

  1. temperatureto reflux
  2. customto evaporate until the total volume was approximately 30 mL
  3. temperatureThe reaction was refluxed for 5 hours more
  4. customa white solid precipitated
  5. temperatureThe reaction was cooled
  6. filtrationthe solid collected by filtration
  7. washwashed with a minimum of MeOH
  8. customdried on the pump

Sources & evidence

ORD record
ord-e3771936519c4ea5ace24e26dbfe8053
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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