Ethanol → HCID 20217537, compound

HRID 235858Notes

Reaction equation

HRID 235858 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.[NH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[N:13][C:14]([O:20][CH3:21])=[CH:15][CH:16]=2)[N:11]=1.C(O)C>O>[CH3:21][O:20][C:14]1[N:13]=[C:12]2[C:17]([CH:18]=[CH:19][C:10]([NH:9][C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[O:8])=[N:11]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 69192-Furancarboxylic acidHCID 217930277-methoxy-1,8-Naphthyridin-2-amine

Product 1

HCID 20217537HCID 20217537, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with 2-furancarboxylic acid (8.95 g), N,N'-carbonyldiimidazole (12.8 g) and 2-amino-7-methoxy-1,8-naphthyridine (10.5 g). The product produced by precipitation in water (15.5 g; m.p. 199° C.) is dissolved in boiling ethanol (500 cc). After 2 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with ethanol (2×10 cc) and dried at 45° C. under reduced pressure (0.067 kPa). N-(7-Methoxy-1,8-naphthyridin-2-yl)-2-furancarboxamide (13.5 g) is produced, m.p. 201° C.

Workup

  1. dissolutionis dissolved
  2. customthe crystallised solid is separated by filtration
  3. washwashed with ethanol (2×10 cc)
  4. customdried at 45° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-fb9827c73e1245b394d8bb3d31b4abe0
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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